Directory UMM :wiley:Public:journals:jcc:suppmat:20:
Supplementary Material Tables for:
MMFF VII. Characterization of MMFF94, MMFF94s, and Other Widely Available
Force Fields for Conformational Energies and for Intermolecular-Interaction
Energies and Geometries.
THOMAS A. HALGREN
Molecular Systems, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065
Contents:
Comparisons of ab initio "MP4SDQ/TZP" and calculated force-field results for 147 conformational energies:
• Table SM-I
Detailed comparisons of calculated force-field intermolecular interaction energies and geometries to scaled quantum mechanical results:
• MMFF94 (Table SM-II)
• MMFF94s (Table SM-III)
• CFF95 (Table SM-IV)
• CVFF (Table SM-V)
• MSI CHARMm (Table SM-VI)
• CHARMM 22 (Table SM-VII)
• AMBER* (Table SM-VIII)
• OPLS* (Table SM-IX)
• MM2* (Table SM-X)
• MM3* (Table SM-XI)
TABLE SM-I. ________________________________________________________________________________________
Comparison of Ab Initio "MP4SDQ/TZP" and Empirical Force Field Conformational Energies (kcal/mol)
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
1.03
1.90
0.41
1.09
1.97
0.44
1.28
2.18
0.40
1.83
3.09
0.95
3.44#
2.46
2.68#
1.57
2.33
0.37
0.41
1.98
-0.98
alanine dipeptide analog, α'- C7eq
0.91
1.08
2.20
4.88
1.08
1.11
1.58
5.24
1.14
1.12
1.83
4.85
-0.16
0.76
1.43
4.54
2.13
2.58#
1.43
7.04#
1.29
1.68
1.72
6.22
0.37
1.69
2.98
4.32
5.24##
5.52##
1.36
---
0.65
0.00
1.16
3.60
alanine dipeptide analog, β2' - C7eq
2.76
---
2.47
---
---
---
1.84
---
---
alanine dipeptide analog, αL - C7eq
N-OH,N-methylacetamide,
o-n-c=o cis - trans
N-OH,N-Et acetamide,
[o-n-c=o trans, c-c-n-o g] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH,N-Et acetamide,
[o-n-c=o trans, c-c-n-o trans] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH,N-Et acetamide,
[o-n-c=o cis, c-c-n-c(=o) sk] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH, N-Me propionamide,
[o-n-c=o trans, c-c-c=o cis] [o-n-c=o cis, c-c-c=o cis]
4.10
4.28
3.87
---
---
---
---
---
1.16#
0.04
-0.19
0.01
1.95#
---
---
0.24
0.53
0.14
-1.97#
2.55#
---
---
1.50
---
1.56
-2.39##
---
---
9.32##
---
---
0.08
---
0.27
---
0.04
---
---
---
---
0.04
0.24
0.08
-2.21#
5.17##
9.46##
---
---
Conformational comparison
Amides:
N-methylformamide, cis - trans
N-methylactamide, cis - trans
N-formylformamide,
o=c-n-h cis,trans - cis,cis
glycine dipeptide analog, C5 - C7
alanine dipeptide analog, C5 - C7eq
alanine dipeptide analog, C7ax - C7eq
OPLS*
-5.40## -5.03## -9.38##
3.82##
4.81## 10.08##
MM2*
MM3*
0.46
1.74
-1.10#
1.50
2.31
1.72
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
0.96
1.24
1.07
0.72
1.24
1.09
0.26
0.26
---
alanine dipeptide, α' - C7eq
1.66
1.64
2.20
5.35
1.40
1.42
1.84
5.66
1.62
1.68
2.26
5.47
1.08
1.79
1.17
5.34
2.55
2.93
1.84
7.30#
alanine dipeptide, β2 - C7eq
3.20
---
3.06
---
alanine dipeptide, αL - C7eq
4.25
4.74
4.75
4.79
5.86
0.85
0.35
4.89
5.87
0.84
1.91#
1.64
0.21
2.22
1.65
Conformational comparison
N-OH, N-Me propionamide,
[o-n-c=o trans, c-c-c=o sk] [o-n-c=o cis, c-c-c=o cis]
N-OH, N-Me propionamide,
[o-n-c=o cis, c-c-c=o sk] [o-n-c=o cis, c-c-c=o cis]
glycine dipeptide, C5 - C7
alanine dipeptide, C5 - C7eq
alanine dipeptide, C7ax - C7eq
Carboxylic Acids:
formic acid, trans - cis
acetic acid, trans - cis
propanoic acid, c-c-c=o sk - cis
gyloxylic acid,
[o=c-c=o trans, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
glycolic acid, o=c-c-o sk - cis
propenoic acid, c=c-c=o trans - cis
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,cis] [o=c-c=o trans, o=c-o-h trans,trans]
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,trans] [o=c-c=o trans, o=c-o-h trans,trans]
-2.41##
3.42#
AMBER*
OPLS*
MM3*
---
---
2.19
---
---
-1.20#
-0.69#
2.19
---
-0.70#
0.44
2.95
5.48
5.65##
6.05##
1.53
---
1.25
0.56
1.34
4.26
---
---
---
---
---
---
---
---
---
---
---
4.89
5.87
0.84
1.91#
4.48
6.05
0.90
2.94#
5.97
4.76
0.80
0.89
6.55#
7.23
-0.22
1.07
0.80
0.25
0.97
0.80
0.25
0.97
2.57
-2.76## -0.71#
0.70
-0.39
-0.03
6.22## 7.46## 0.01#
1.90
1.90
3.94##
4.05##
5.17## 11.29##
MM2*
1.34
7.64# 11.38## 4.89
6.67
13.66## 5.70
-0.10
0.52
0.71
5.08## -5.68## -0.49
-3.50## 0.94
2.88
-0.14
-0.05
-1.17
9.84## -8.85## -1.74##
6.30## -2.61## -0.34#
Conformational comparison
pyruvic acid,
[o=c-c=o cis, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
Esters:
methyl formate, o=c-o-c trans - cis
methyl acetate, o=c-o-c trans - cis
vinyl formate, c=c-o-c cis - trans
ethyl formate, c-o-c-c g - a
isopropyl formate, c-c-o-c g,g - g,a
phenyl acetate, o=c-o-c cis - trans
methyl glycolate, o=c-c-o sk - cis
Congujated systems:
1,3-butadiene, g - s-trans
2-methyl-1,3-butadiene, g - s-trans
2-methyl-but-1-ene-3-one,
c=c-c=o cis - trans
2-methylpropenamide, c=c-c=o cis - sk
propenamide, c=c-c=o sk - cis
but-1-ene-3-one, c=c-c=o cis - trans
acrolein, c=c-c=o cis - trans
2-methylpropenal, c=c-c=o cis - trans
2-methylpropenoic acid,
c=c-c=o cis - trans
1,3-pentadiene,
[c=c-c=c g, c-c=c-c trans] [c=c-c=c s-trans, c-c=c-c trans]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
1.67
2.42
2.42
2.97
2.48
1.52
5.65
8.21
2.79
0.34
2.43
4.30
1.48
5.28
8.27
2.83
0.44
2.43
4.50
2.43
5.28
8.27
2.83
0.44
2.43
4.50
2.43
5.09
8.67
--0.67
2.16
2.58#
2.40
2.39
2.20
2.08
2.46
2.12
1.90
2.46
2.12
1.90
3.39
2.79
-0.42#
1.05
0.61
0.43
2.03
3.14
0.60
1.04
0.57
0.28
2.05
3.15
0.62
1.00
0.60
0.28
2.05
3.15
0.62
-0.42
6.08## -3.13## 0.16
0.31
-3.02## -1.77# -2.26#
0.69
0.58
0.67
1.43
1.59
2.47
2.03
1.69
-0.07## 5.50#
1.40#
0.64#
-0.45
0.71
-0.52
0.38
2.43
2.46
2.46
3.24
5.54
9.09
4.79#
--5.58##
1.32#
-3.25##
2.39
1.95
2.46
2.56
OPLS*
4.42#
1.34## 0.87##
7.42
7.47
----0.99
0.69
2.65
2.84
2.06#
4.93
0.35
-0.03#
2.45
3.29
-0.57#
2.70
2.80
1.85
1.37
3.19
MM2*
MM3*
-4.13## -0.16#
5.61
6.68#
2.84
0.27
0.74#
8.80##
2.22
2.18##
7.85
--0.23
1.60
1.28##
2.84
2.74
2.49
1.66
1.72
1.63
1.95
2.90#
-0.84
0.50
1.64
3.25
-1.18#
1.04
-0.79
0.71
1.98
3.46
1.30
2.83
1.83
Conformational comparison
1,3-pentadiene,
[s-trans, c-c=c-c cis] [s-trans, c-c=c-c trans]
Aldehydes and ketones:
propionaldehyde, c-c-c=o sk - cis
2-butanone c-c-c=o sk - cis
methyl ispropyl ketone,
o=c-c(ch3)2-h cis - trans
butyraldehyde, c-c-c-c g - a
but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk+, c-c-c=o sk+]
but-3-enal,
[c=c-c-c sk-, c-c-c=o sk+] [c=c-c-c sk+, c-c-c=o sk+]
3-methyl-but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk, c-c-c=o sk]
isobutyraldehyde, h-c(=0)-c-h a - g
2-formylpropanal, o-c-c-c(=o) a - g
4-oxobutanal (o=c-c-c, c-c-c=o cis, cis),
c-c-c-c s-trans - g
2,3-butanedione, c-c-c-c g - s-trans
Halides:
1,2-difluoroethane, a - g
1,2-dicloroethane, g - a
1-fluoropropane, a - g
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
1.27
2.11
2.11
2.15
0.70
1.29
1.97
2.23
1.12
0.83
0.98
0.69
0.53
0.83
0.89
0.53
0.83
0.89
1.09
1.35
1.24
0.32
0.19
0.87
1.65
1.73
1.65
-0.46
-0.04
0.40
0.90
1.57
1.36
1.10
1.61
1.53
0.14
0.20
0.11
-0.05
0.11
-0.05
0.87
---
0.89
1.16
1.27
-0.96
1.08
-0.11
0.84
0.95
0.91
2.11#
0.29
0.98
0.98
0.65
0.71
0.51
0.62
0.07
0.51
0.43
0.72
0.72
0.06
1.34
0.08
1.31
1.25
2.68#
0.37
0.18
0.70
0.56
0.14
0.77
0.56
0.14
0.77
0.97
0.01
-1.34#
-0.49
-1.94#
0.03
0.99
0.25
-0.24
1.16
-0.33
-1.37#
5.40
---
---
3.51#
4.66
---
---
0.58
1.29
0.03
0.63
1.24
0.06
0.63
1.24
0.06
-1.57#
1.22
-0.93
1.05
1.47
-0.12
-1.16#
1.13
0.03
-0.93#
0.87
-0.41
0.04
1.58
-3.85## -2.60#
-0.98#
2.14
7.12#
0.01
1.13
-0.08
2.88#
0.04
1.95
-0.10
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.03
0.00
0.00
1.03
0.15
0.07
0.39
0.23
0.29
2.03
2.03
2.27
1.62
2.08
1.78
4.23#
-0.96#
-0.68#
2.00
2.00
2.12
2.67
3.82#
---
-0.09#
1.03
1.73
1.94
1.94
6.58##
2.63
1.96
1.89
2.60
1.99
1.30
1.81
1.81
1.88
2.37
0.97
1.70
2.27
1.63
2.44
2.11
2.11
2.54
3.37
2.95
1.93
2.99
2.26
0.63
2.25
0.50
2.97
0.50
2.97
0.04
1.96
-0.65
-0.67
-3.98## 2.34
0.41
2.86
0.69
2.84
0.75
2.94
Cations:
N-proplyamine cation, c-c-c-n g - a
ethylguanidine cation, c-c-n=c g - a
0.07
0.62
0.03
0.38
0.03
0.38
0.29
---
-0.32
-1.37#
-0.65
-0.18
0.34
0.33
0.99
0.11
1.12
---
Amines:
propylamine, c-c-c-n g - a
0.33
0.55
0.55
0.00
0.37
-1.08
0.34
0.87
0.87
Conformational comparison
1-chloropropane, g - a
Imines, guanidines, and amidines
formamidine (N puckered),
h-n=c-n cis - trans
N-methylformamidine (N puckered),
n-c=n-c cis - trans
butadiene schiff base,
[c=c-c=n s-cis, h-n=c-c trans] [c=c-c=n s-trans, h-n=c-c cis]
Ketals, acetals, and hemiacetals:
2-methoxytetrahydropyran,
[eq, me-o-c-c a] - [ax, me-o-c-c a]
2,4-dioxapentane,
[c-o-c-o g, o-c-o-c a] [c-o-c-o g+, o-c-o-c g+]
2,5-dimethyl-1,3-dioxane, 5-ax - 5-eq
methoxymethanol,
[c-o-c-o g+, o-c-o-h g-] [c-o-c-o g+, o-c-o-h g+]
-3.12##
Conformational comparison
isopropylamine,
[C1, h-c-n-lp g] [Cs, h-c-n-lp a]
cyclohexylamine, ax - eq
piperidine, n-h ax - eq
N-methylpiperidine, ax - eq
ethylamine, c-c-n-lp a - g
3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
3-aminopropene,
[c=c-c-n sk, c-c-n-lp a] [c=c-c-n sk, c-c-n-lp g]
2-methyl,3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
ethylenediamine,
[n-c-c-n a, c-c-n-lp g+, g+] [n-c-c-n g+, c-c-n-lp g+, g+]
methylethylamine N-oxide, c-n-c-c g - a
methylethylhydroxylamine, c-n-c-c g - a
ethylamine N-oxide, o-n-c-c a - g
ethylhydroxylamine, o-n-c-c a - g
Alcohols:
ethanol, a - g
n-propanol,
[c-c-c-o g-, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.50
0.45
0.45
0.16
-0.07
0.23
0.00
0.15
0.22
0.69
0.78
3.58
0.08
0.50
0.67
0.90
3.28
0.44
0.51
0.67
0.90
3.28
0.44
0.51
0.83
0.05
3.25
0.20
2.44#
1.78
0.13
2.70
0.22
0.00
-0.74
0.14
1.26#
0.26
-0.84
0.62
-0.04
2.32
0.00
-1.07#
1.38
0.31
2.53
0.14
0.71
1.23
0.31
2.31
0.12
1.82
0.15
0.65
0.65
-0.17
-0.21
-0.18
0.68
-0.30
-0.08
0.67
0.61
0.61
1.19
0.47
0.32
-0.93#
1.03
1.75
1.39
1.45
1.45
0.84
1.48
1.20
0.59
1.38
1.69
0.68
0.20
1.41
2.25
0.73
0.05
1.41
2.25
0.73
0.05
-0.73#
1.63
-1.61#
-0.57
3.62#
1.76
1.61
2.98#
0.06
0.23
-0.18
0.58
-0.18
0.58
-0.37
-0.42
-0.23
0.02
12.94## 21.84##
1.23
1.17
0.68
0.55
--1.61
---0.28
--1.20
---0.05
---------
-0.36
-0.76
0.00
0.28
-0.60
0.36
-0.41
0.60
Conformational comparison
n-propanol,
[c-c-c-o g+, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
n-propanol,
[c-c-c-o a, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
n-propanol,
[c-c-c-o g, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
isopropanol, h-c-o-h a - g
cyclopentanol, eq C s - ax C1
cyclopentanol, ax C s- ax C1
cyclopentanol, eq C 1 - ax C1
cyclohexanol, eq Cs - eq C1
cyclohexanol, ax Cs - eq C1
cylohexanol, ax C1 - eq C1
vinyl alcohol, c=c-o-h trans - sk
benzyl alcohol, h-o-c-c a - g
propen-3-ol,
[c=c-c-o sk, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
propen-3-ol,
[c=c-c-o cis, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
2-me-propen-3-ol,
[c=c-c-o c, c-c-o-h a] [c=c-c-o s, c-c-o-h a]
sec-butanol, ga/ga - ga/aga
sec-butanol, ga/gg - ga/ag
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
0.05
0.24
0.24
0.01
-0.43
0.20
-0.17
-0.17
-0.49
0.10
0.12
0.12
0.20
1.11
1.05
1.14
0.18
1.14
0.33
1.43
1.13
1.24
0.17
0.82
0.59
0.47
0.20
1.01
0.32
1.43
1.59
1.10
1.11
OPLS*
MM2*
MM3*
-0.62
0.28
0.36
0.35
-0.16
-0.30
0.00
-0.60
-0.42
-0.23
-0.29
-0.81
0.28
-0.30
-0.06
0.17
0.82
0.59
0.47
0.20
1.01
0.32
1.43
1.59
1.10
0.40
-0.27
-0.33
-0.53#
0.38
-0.49#
0.24
1.58
1.38
0.82
0.02
---0.94#
-0.62#
0.06
0.58
0.40
0.66
2.97#
2.43
0.25
-0.36
--0.70
0.15
-0.87#
-0.57
-0.81#
0.81
1.07
0.00
-0.07
0.00
-0.07
0.00
0.50
0.50
-0.69#
1.23
0.19
0.61
0.40
0.82
-0.23
0.62
1.46
0.58
1.75
1.22
1.20
0.68
0.89
1.35
-0.15
0.77
2.43
0.74
-0.09#
1.33
1.12
1.13
1.13
3.39#
0.49
-0.08
-1.06#
0.83
2.76#
0.38
0.47
0.47
0.94
0.39
-0.71
-1.57#
-0.10
1.53
0.10
0.18
0.33
0.11
0.33
0.11
-0.62
0.23
0.23
-0.32
-0.30
0.05
0.00
0.00
0.07
0.64
0.24
0.69
AMBER*
Conformational comparison
sec-butanol, ag/ag - ga/ag
sec-butanol, ag/ga - ga/ag
sec-butanol, ag/gg - ga/ag
sec-butanol, gg/ag - ga/ag
sec-butanol, gg/ga - ga/ag
sec-butaone, gg/gg - ga/ag
1,2-ethanediol,
[h-o-c-c a, o-c-c-o a, c-c-o-h a] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
1,2-ethanediol,
[h-o-c-c g-, o-c-c-o g+, c-c-o-h g+] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
1,2-ethanediol,
[h-o-c-c g+, o-c-c-o g-, c-c-o-h g+] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
0.48
0.29
0.56
0.75
0.57
1.13
2.71
0.47
0.46
0.59
0.72
0.66
1.14
2.91
0.47
0.46
0.59
0.72
0.66
1.14
2.91
0.57
0.74
1.15
0.87
0.68
0.56
0.70#
1.02
1.06
0.87
0.79
0.43
1.01
2.45
0.93
0.85
1.07
0.40
0.20
0.33
5.69#
0.49
1.15
1.15
1.45
0.79
1.41
1.58
1.58
1.92
1.17
OPLS*
MM2*
MM3*
0.71
0.71
0.71
1.00
1.00
1.00
17.30##
0.53
0.53
1.14
0.82
0.90
1.54
2.30
0.49
0.50
1.14
0.98
0.97
2.06
0.80#
0.29
---
1.47
---
0.37
---
1.50
---
1.74
1.07
1.77
1.48
0.60#
1.49
Ethers:
methyl ethyl ether, g - a
methyl vinyl ether, c=c-o-c skew - cis
diethyl ether,
[c-c-o-c a, c-o-c-c g] [c-c-o-c a, c-o-c-c a]
methoxycyclohexane, eq Cs - ax C1
methoxycyclohexane, eq C1 - ax C1
methyl isopropyl ether, h-c-o-ch3 a - g
1.41
2.27
1.48
1.50
2.22
1.52
1.50
2.22
1.52
2.10
0.01
1.91
1.95
-0.41
1.88
1.95
-0.41
1.88
2.19
0.11
2.10
1.56
-0.70
1.91
2.76
0.34
2.25
2.08
-0.37
2.20
1.53
-0.56
1.73
1.80
-0.76
2.12
Alkanes:
butane, g - a
0.65
0.78
0.78
0.89
0.78
0.39
0.95
0.86
0.81
1.46
-3.10##
1.37
1.53
2.10
1.55
1.79
1.85
-2.90## -3.94##
1.83
1.84
Conformational comparison
cyclohexane, twist-boat - chair
methylcyclohexane, ax - eq
2,3-dimethylbutane, h-c2-c3-h g - a
cyclooctane, D4d crown - Cs boat-chair
cyclooctane,
C2 twist-boat-chair - Cs boat-chair
cyclooctane, S4 - Cs boat-chair
methylcyclobutane, ax - eq
cyclononane, C2 [144] - D3 [333]
cyclononane, C2 [225] - D3 [333]
cyclononane, C1 [234] - D3 [333]
Alkenes:
1-butene, c=c-c-c cis - sk
1-pentene (c=c-c-c skew),
c-c-c-c g - a
2-methyl-1-butene, c=c-c-c skew - cis
1,4-pentadiene,
c=c-c-c sk+,sk- - sk-,sk2-butene, cis - trans
2-pentene,
[c-c=c-c cis, c-c-c=c sk] [c-c=c-c trans, c-c-c=c sk]
Thiols, sulfides, and disulfides:
ethanethiol, c-c-s-h a - g
ethyl methyl disulfide, c-c-s-s a - g
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
6.14
1.69
0.04
2.00
1.71
5.93
1.37
-0.23
1.44
1.99
5.93
1.37
-0.23
1.44
1.99
7.08
1.84
0.13
1.21
2.30
6.72
1.80
0.40
0.45#
1.88
2.97
0.77
1.97
0.99
3.65
3.27
0.78
1.41
1.21
3.81
3.27
0.78
1.41
1.21
3.81
0.16#
1.21
1.02
-1.63#
2.03#
4.48#
0.06
0.37#
1.12
3.45
0.26
0.61
0.26
0.51
0.26
0.51
0.72
0.90
0.46
-0.10
0.66
0.11
0.02
0.33
-0.03
0.43
-0.03
0.43
-0.07
0.33
-0.93
0.19
1.27
1.31
1.35
1.33
1.35
1.33
1.43
1.35
0.74
0.76
0.68
0.76
0.68
0.76
0.33
-0.31
OPLS*
MM2*
MM3*
5.79
0.90
-0.22
0.83
1.77
6.77
1.78
-0.48
-1.67##
1.20
5.36
1.78
0.15
0.96
1.66
5.76
1.77
0.38
1.12
1.85
3.63
0.17
0.53
1.07
3.66
6.51##
0.63
-1.02#
0.80
4.31
3.12
0.58
0.77
0.75
3.16
2.62
0.92
1.15
0.84
3.04
1.00
0.60
0.49
0.78
0.68
0.42
-0.97
0.44
-0.98
0.25
-0.06
0.07
-0.38
0.27
1.61
1.61
1.55
1.43
2.49
2.39
1.43
1.29
1.02
0.99
-0.78#
0.11
-0.20
-1.29#
0.00
0.04
0.28
-0.19
-0.04
0.05
AMBER*
Conformational comparison
1-propanethiol,
[s-c-c-c g-, h-s-c-c g+] [s-c-c-c a, h-s-c-c g]
1-propanethiol,
[s-c-c-c g, h-s-c-c a] [s-c-c-c a, h-s-c-c g]
1,2-ethanedithiol,
[all anti] [h-s-c-c a,g+, s-c-c-s g-]
1,2-ethanedithiol,
[h-s-c-c a,a, s-c-c-s g] [h-s-c-c a,g+, s-c-c-s g-]
methyl propyl sulfide,
[c-s-c-c g-, s-c-c-c g-] [c-s-c-c g, s-c-c-c a]
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c g] [c-s-c-c g, s-c-c-c a]
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c a] [c-s-c-c g, s-c-c-c a]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.30
0.37
0.37
1.59
-0.84
1.51
0.48
0.84
1.04
1.23
0.95
0.95
2.26
-1.65#
1.53
0.48
0.92
0.65
0.86
1.17
1.17
0.15
-0.95#
6.92##
5.17#
-0.92#
-1.71#
1.77
2.24
2.24
1.71
0.26#
1.62
5.51##
0.68
0.34
0.09
0.05
0.05
1.56
-0.08
1.21
0.12
0.58
0.61
0.66
0.60
0.60
-0.03
0.18
0.94
-0.24
0.24
0.51
0.25
0.33
0.33
-1.66#
0.23
-0.24
-0.43
-0.39
-0.18
a For
the OH14 conformers (sec-butanol), in the conformational designations "wx/yz", "w" indicates the conformation of the c-c-c-o
angle, "x" that of the c-c-c-c angle,"y" that of the h-o-c-ch2 angle, and "z" that of the h-o-c-ch3 angle.
# Denotes a conformational enregy that differs from the reference "MP4SDQ/TZP" value by > 1.5 kcal/mol.
## Denotes a conformational enregy that differs from the reference "MP4SDQ/TZP" value by > 3 kcal/mol.
TABLE SM-II. _________________________________________________________________________________
MMFF94 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.61
-4.91
-0.14
0.11
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.33
-6.15
-6.04
-5.98
-8.45
-5.08
-8.48
-5.46
-3.78
-17.09
-0.23
0.00
0.05
-0.14
-0.35
0.10
-0.30
-0.30
0.22
0.01
H3 CCOOH...OHH (13)
-10.94
-11.70
-0.76
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-6.10
-1.20
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.80
-6.84
-2.62
-6.74
0.40
-0.45
1.20
-0.93
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.75
2.78
2.78
2.73
2.75
2.73
2.77
2.69
2.83
2.68
2.81
2.88
2.62
2.62
2.64
2.77
2.61
2.60
2.94
2.79
2.86
3.20
2.87
2.73
2.95
2.71
0.02
0.19
0.19
0.02
0.03
0.02
0.06
0.02
0.04
0.02
0.02
0.10
0.05
0.05
0.07
0.16
0.07
-0.02
-0.04
-0.17
-0.04
-0.01
0.14
-0.03
0.17
0.00
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
2.19
2.19
1.76
1.76
1.74
1.81
1.72
1.89
1.69
1.87
1.97
1.63
1.63
1.67
2.11
1.61
1.92
2.02
2.69
2.02
2.43
1.94
1.75
2.12
1.74
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
170.4
117.0
117.0
168.7
179.9
177.0
166.7
167.5
159.9
176.1
160.4
155.4
169.2
169.2
163.4
122.8
175.4
123.9
155.7
85.4
142.6
135.5
159.0
177.6
142.0
170.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-7.06
-6.86
-8.19
-12.26
-0.19
-0.89
-0.16
2.52
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.69
-9.08
-5.62
0.43
-1.38
-1.76
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-8.07
-6.94
-7.99
-3.95
-3.02
-0.17
-0.89
0.22
0.15
0.49
H2 NH...NH3 , linear Cs (33)
-3.38
-3.67
-0.29
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.83
-6.70
-7.91
-7.93
-6.51
-6.28
-7.10
-10.65
0.39
0.37
-0.91
-0.16
-0.18
-0.39
-0.47
0.38
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-7.95
-7.47
-1.21
0.49
Vinylamine...OH2 (44)
-3.80
-4.61
-0.81
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.71
2.84
2.71
2.81
2.81
2.76
2.76
3.61
3.61
2.71
2.82
2.70
2.85
3.11
3.11
3.03
3.03
2.80
2.82
2.82
2.75
2.86
2.86
2.79
2.97
2.76
2.74
2.90
2.94
2.87
-0.03
-0.03
0.00
0.06
0.06
-0.03
-0.07
-0.05
-0.06
0.00
-0.01
0.08
0.03
0.10
0.10
-0.12
-0.12
0.00
0.02
0.04
0.01
0.05
0.04
0.02
0.15
0.06
-0.02
0.02
0.18
-0.17
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.73
1.82
1.73
1.79
1.79
1.74
1.76
3.49
3.49
1.73
1.80
1.72
1.87
2.40
2.40
2.00
3.36
1.82
1.84
1.81
1.81
1.84
1.84
1.85
2.09
1.80
1.77
1.98
2.11
1.85
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.1
176.9
174.2
173.4
173.4
174.4
165.3
88.5
88.4
174.8
175.4
175.8
175.8
125.4
125.4
178.1
62.7
173.9
173.1
175.6
158.6
179.7
180.0
158.9
142.8
162.0
167.6
148.1
141.1
173.3
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.86
-2.91
-3.48
-0.24
0.02
0.08
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-3.22
-2.71
0.56
-0.05
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-1.25
-2.00
-11.58
-1.25
-0.29
0.27
0.36
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-10.61
-14.87
0.08
0.61
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-4.48
-2.84
-3.43
-21.17
-19.02
0.39
0.25
-0.31
-1.87
-0.54
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-17.60
-18.75
-19.71
-0.65
-1.77
-0.12
Formaldehydeiminium...OH2 (65)
OHH...(-)O2 CCH3 , bidentate (66)
-19.98
-21.85
-21.65
-22.62
-1.67
-0.77
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.66
2.77
2.78
2.87
3.38
3.35
3.35
3.55
3.69
3.69
4.37
4.02
3.49
2.66
3.02
2.64
2.59
2.74
2.79
2.88
2.66
3.35
3.00
2.62
2.78
2.78
2.62
2.61
2.78
2.78
2.65
2.74
2.74
-0.06
0.05
0.23
0.23
0.17
0.10
0.10
-0.19
-0.13
0.02
0.03
0.12
0.01
0.10
0.11
0.13
0.22
-0.04
0.01
0.00
-0.08
-0.07
-0.07
-0.08
-0.10
-0.05
-0.05
-0.01
-0.03
-0.03
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
1.78
2.06
2.08
1.85
2.03
2.38
3.62
2.58
3.03
3.34
3.55
2.70
2.55
1.66
2.43
1.65
1.66
2.10
1.94
2.10
1.69
2.45
1.97
1.57
1.87
1.87
1.59
1.57
1.89
1.89
1.61
1.87
1.87
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
163.4
142.9
141.8
172.8
172.8
170.8
66.4
174.6
126.8
103.6
144.2
167.3
163.2
174.3
115.2
178.6
154.6
117.6
143.2
135.1
172.7
153.9
173.9
176.7
146.8
146.8
173.4
177.2
143.6
143.6
176.6
145.7
145.7
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-III. _________________________________________________________________________________
MMFF94s vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.61
-4.91
-0.14
0.11
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.33
-6.15
-6.04
-5.98
-8.45
-5.08
-8.48
-5.46
-3.78
-17.09
-0.23
0.00
0.05
-0.14
-0.35
0.10
-0.30
-0.30
0.22
0.01
H3 CCOOH...OHH (13)
-10.94
-11.70
-0.76
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-6.10
-1.20
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.80
-6.84
-2.62
-6.74
0.40
-0.45
1.20
-0.93
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.75
2.78
2.78
2.73
2.75
2.73
2.77
2.69
2.83
2.68
2.81
2.88
2.62
2.62
2.64
2.77
2.61
2.60
2.94
2.79
2.86
3.20
2.87
2.73
2.95
2.71
0.02
0.19
0.19
0.02
0.03
0.02
0.06
0.02
0.04
0.02
0.02
0.10
0.05
0.05
0.07
0.16
0.07
-0.02
-0.04
-0.17
-0.04
-0.01
0.14
-0.03
0.17
0.00
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
2.19
2.19
1.76
1.76
1.74
1.81
1.72
1.89
1.69
1.87
1.97
1.63
1.63
1.67
2.11
1.61
1.92
2.02
2.69
2.02
2.43
1.94
1.75
2.12
1.74
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
170.4
117.0
117.0
168.7
179.9
177.0
166.7
167.5
159.9
176.1
160.4
155.4
169.2
169.2
163.4
122.8
175.4
123.9
155.7
85.4
142.6
135.5
159.0
177.6
142.0
170.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-7.06
-6.87
-8.25
-12.26
-0.19
-0.90
-0.22
2.52
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.69
-9.06
-5.33
0.43
-1.36
-1.47
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-8.14
-6.90
-8.30
-4.26
-3.02
-0.24
-0.85
-0.09
-0.16
0.49
H2 NH...NH3 , linear Cs (33)
-3.38
-3.67
-0.29
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.83
-6.70
-7.91
-7.93
-6.51
-6.28
-7.10
-10.68
0.39
0.37
-0.91
-0.16
-0.18
-0.39
-0.47
0.35
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-7.95
-7.02
-1.21
0.94
Vinylamine...OH2 (44)
-3.80
-4.23
-0.43
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.71
2.84
2.70
2.81
2.81
2.76
2.76
3.64
3.64
2.71
2.83
2.70
2.84
3.11
3.11
3.03
3.03
2.80
2.82
2.82
2.75
2.86
2.86
2.79
2.97
2.77
2.74
2.88
3.22
2.88
-0.03
-0.03
0.00
0.06
0.06
-0.03
-0.07
-0.01
-0.02
0.00
-0.01
0.08
0.03
0.10
0.10
-0.12
-0.12
0.00
0.02
0.04
0.01
0.05
0.04
0.02
0.16
0.07
-0.02
0.00
0.46
-0.16
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.73
1.81
1.72
1.79
1.79
1.74
1.75
3.54
3.54
1.73
1.80
1.72
1.87
2.40
2.40
2.00
3.36
1.82
1.84
1.81
1.81
1.84
1.84
1.85
2.13
1.80
1.77
1.88
3.84
1.85
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.1
179.9
174.3
173.4
173.4
174.1
166.8
88.0
88.0
174.9
175.5
177.0
178.2
125.4
125.4
178.1
62.7
173.9
173.1
175.6
158.6
179.7
180.0
158.9
137.8
167.5
167.6
165.7
45.0
176.9
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.54
-2.91
-3.48
0.08
0.02
0.08
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-3.22
-2.71
0.56
-0.05
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-1.25
-2.00
-11.58
-1.25
-0.29
0.27
0.36
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH (55)
-10.69
-15.48
-10.61
-14.87
0.08
0.61
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-4.48
-2.84
-3.43
-21.17
-19.02
0.39
0.25
-0.31
-1.87
-0.54
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-17.60
-18.75
-19.71
-0.65
-1.77
-0.12
Formaldehydeiminium...OH2 (65)
OHH...(-)O2 CCH3 , bidentate (66)
-19.98
-21.85
-21.65
-22.62
-1.67
-0.77
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.66
2.77
2.78
2.88
3.38
3.35
3.35
3.55
3.69
3.69
4.37
4.02
3.49
2.66
3.02
2.64
2.59
2.74
2.79
2.88
2.66
3.35
3.00
2.62
2.78
2.78
2.62
2.61
2.78
2.78
2.65
2.74
2.74
-0.06
0.05
0.23
0.23
0.17
0.10
0.10
-0.19
-0.13
0.02
0.03
0.12
0.01
0.10
0.11
0.13
0.22
-0.04
0.01
0.00
-0.08
-0.07
-0.07
-0.08
-0.10
-0.05
-0.05
-0.01
-0.03
-0.03
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
1.78
2.06
2.08
1.86
2.03
2.38
3.62
2.58
3.03
3.34
3.55
2.70
2.55
1.66
2.43
1.65
1.66
2.10
1.94
2.10
1.69
2.45
1.97
1.57
1.87
1.87
1.59
1.57
1.89
1.89
1.61
1.87
1.87
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
163.4
142.9
141.8
174.9
172.8
170.8
66.4
174.6
126.8
103.6
144.2
167.3
163.2
174.3
115.2
178.6
154.6
117.6
143.2
135.1
172.7
153.9
173.9
176.7
146.8
146.8
173.4
177.2
143.6
143.6
176.6
145.7
145.7
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-IV. _________________________________________________________________________________
CFF95 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-5.40
-4.26
1.07
0.76
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-4.61
-6.53
-5.65
-2.93
-6.28
-3.97
-6.32
-5.37
-3.86
-10.57
1.49
-0.38
0.44
2.91
1.82
1.21
1.86
-0.21
0.14
6.53
H3 CCOOH...OHH (13)
-10.94
-9.00
1.94
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-8.97
2.26
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.20
0.70
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-3.82
0.00
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-3.78
-4.58
-4.58
-3.85
1.42
1.81
-0.76
1.96
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.90
2.88
2.88
2.93
2.84
2.86
3.08
2.88
3.03
2.85
2.90
3.14
2.88
2.88
2.80
3.03
2.80
2.88
3.16
3.03
3.05
3.22
3.03
2.98
4.30
2.98
0.17
0.30
0.30
0.22
0.11
0.15
0.37
0.21
0.24
0.19
0.12
0.36
0.31
0.31
0.22
0.42
0.26
0.27
0.19
0.07
0.15
0.01
0.30
0.22
1.52
0.27
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.93
2.25
2.25
1.97
1.86
1.89
2.11
1.91
2.10
1.87
1.96
2.22
1.91
1.91
1.83
2.48
1.84
2.29
2.21
2.78
2.27
2.42
2.09
2.00
3.49
2.03
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
169.6
121.4
121.4
168.1
179.0
179.0
176.3
173.8
159.3
179.3
162.1
156.6
169.0
169.0
168.3
115.5
167.3
118.3
163.8
95.3
136.5
139.4
160.8
179.2
141.3
166.8
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-4.13
-7.41
-5.67
-10.02
2.74
-1.44
2.36
4.76
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-6.49
-7.88
-5.28
1.63
-0.18
-1.42
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-5.66
-7.43
-7.50
-8.29
-1.29
2.23
-1.38
0.71
-4.19
2.22
H2 NH...NH3 , linear Cs (33)
-3.38
-1.38
2.00
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-3.75
-3.58
-7.81
-6.05
-6.82
-6.28
-4.25
-8.51
3.47
3.50
-0.81
1.72
-0.49
-0.39
2.38
2.52
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.91
-7.00
0.83
0.96
Vinylamine...OH2 (44)
-3.80
-4.33
-0.53
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.99
2.91
2.95
2.99
2.99
2.98
2.95
3.84
3.84
2.95
2.90
2.82
2.82
3.16
3.16
3.20
3.20
2.97
3.04
2.85
3.14
2.88
2.89
3.20
2.98
2.90
2.90
3.01
2.97
2.98
0.25
0.04
0.25
0.23
0.23
0.19
0.12
0.19
0.17
0.24
0.06
0.20
0.01
0.15
0.15
0.05
0.05
0.18
0.24
0.06
0.41
0.07
0.07
0.42
0.17
0.20
0.14
0.13
0.20
-0.06
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
2.01
1.89
1.98
1.97
1.97
2.06
1.95
3.69
3.69
1.98
1.88
1.88
3.49
2.42
2.42
2.19
3.25
2.00
2.08
1.82
2.25
1.84
1.85
2.32
2.11
1.92
1.92
2.10
2.06
1.97
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
179.9
179.1
172.2
177.5
177.5
149.8
167.4
91.1
91.1
172.1
177.0
160.3
40.3
130.0
130.0
177.7
78.4
173.6
169.3
178.0
150.0
175.7
180.0
148.8
142.5
171.2
179.6
148.2
152.8
177.0
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-5.17
-2.19
-2.05
-0.55
0.74
1.51
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.71
-4.36
2.07
-1.70
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-4.38
-1.23
-2.75
-6.04
-2.18
-0.26
-0.48
5.90
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-7.20
-21.09
3.49
-5.60
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.51
0.90
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-1.69
-1.09
-1.18
-18.81
-16.40
3.17
1.99
1.94
0.49
2.08
Imidazolium...OH2 (62)
OHH...(-)O2 CCH3 , bidentate (66)
-16.95
-21.85
-15.95
-17.22
1.00
4.63
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.77
2.78
2.93
3.58
3.28
3.28
3.47
3.63
3.63
4.40
3.77
3.09
2.86
3.27
2.87
3.45
2.73
2.84
3.58
3.09
4.43
3.36
2.74
2.96
2.96
2.78
2.86
2.86
-0.01
0.25
0.16
0.16
0.09
0.04
0.04
-0.16
-0.38
-0.38
0.23
0.37
0.24
0.96
0.09
0.18
0.92
0.39
1.10
0.36
0.04
0.11
0.11
0.07
0.09
0.08
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
2.06
2.08
1.91
2.84
2.30
3.64
2.50
3.57
2.91
3.77
3.02
2.13
1.88
2.74
1.89
3.83
1.72
1.87
3.99
2.13
3.81
2.35
1.74
2.02
2.02
1.74
2.00
2.00
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
142.9
141.8
175.0
113.4
178.2
60.6
172.9
85.7
131.4
125.0
114.4
167.5
177.6
112.8
177.3
59.9
170.5
173.0
58.3
169.7
125.0
179.8
167.9
152.4
152.4
172.4
143.9
143.9
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-IV. _________________________________________________________________________________
CVFF vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.40
-4.74
0.07
0.28
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-4.41
-6.78
-5.03
-5.09
-7.57
-4.18
-7.33
-4.31
-3.87
-11.14
1.69
-0.63
1.06
0.75
0.53
1.00
0.85
0.85
0.13
5.96
H3 CCOOH...OHH (13)
-10.94
-8.82
2.12
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.31
1.92
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.24
0.66
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.31
-5.49
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.85
-6.19
-3.20
-6.01
0.36
0.20
0.62
-0.20
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.76
2.81
2.81
2.81
2.66
2.69
2.79
2.67
2.83
2.66
2.81
2.93
2.66
2.66
2.66
3.00
2.65
2.74
3.52
2.80
2.74
4.83
2.79
2.75
4.04
2.75
0.03
0.23
0.23
0.09
-0.06
-0.02
0.08
0.01
0.05
0.00
0.02
0.15
0.09
0.09
0.08
0.39
0.11
0.13
0.55
-0.15
-0.16
1.62
0.06
-0.01
1.27
0.03
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.79
2.17
2.17
1.85
1.68
1.72
1.82
1.71
1.88
1.68
1.85
2.01
1.70
1.70
1.70
2.40
1.68
2.05
3.02
1.83
2.05
5.72
1.84
1.77
4.34
1.78
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
173.7
122.3
122.3
168.0
176.0
174.9
173.5
169.3
167.9
177.2
167.5
158.4
171.7
171.7
168.5
119.5
170.4
126.9
113.9
177.7
126.9
21.0
165.6
176.7
65.9
174.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-5.30
-4.19
-6.80
-6.53
1.57
1.78
1.23
8.25
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-5.23
-5.69
-4.84
2.89
2.01
-0.98
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-7.18
-4.46
-8.40
-9.06
-0.46
0.72
1.59
-0.19
-4.97
3.05
H2 NH...NH3 , linear Cs (33)
-3.38
-0.50
2.88
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-6.33
-5.89
-6.63
-11.03
-1.99
-4.05
-2.59
-2.28
-3.36
-3.49
5.23
3.02
3.74
3.61
3.27
7.54
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-3.00
-5.74
3.74
2.22
Vinylamine...OH2 (44)
Aniline...OH2 (45)
HSH...OH2 (46)
-3.80
-4.62
-2.93
-1.76
-2.82
-0.98
2.03
1.80
1.95
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.94
3.33
2.76
3.07
2.74
3.00
3.00
3.08
3.02
4.00
4.00
2.73
3.05
2.64
2.65
3.69
3.69
3.69
3.69
3.18
3.07
3.09
3.11
3.48
3.21
3.18
3.17
3.16
3.16
3.15
3.12
3.48
0.02
0.20
0.04
0.24
0.24
0.29
0.19
0.35
0.33
0.02
0.21
0.02
-0.17
0.69
0.69
0.53
0.53
0.39
0.27
0.28
0.29
0.70
0.40
0.48
0.41
0.28
0.40
0.11
0.18
0.15
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
2.20
2.29
1.79
2.04
1.77
1.97
1.97
2.28
2.00
3.82
3.82
1.76
2.02
1.68
3.31
2.92
2.92
2.66
3.80
2.22
2.10
2.06
2.07
3.26
2.28
2.25
2.23
2.19
3.80
2.12
2.09
2.94
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.2
175.3
179.2
176.8
175.6
175.9
175.9
133.4
168.8
92.7
92.7
172.1
169.3
168.0
40.6
132.8
132.8
176.0
76.0
173.1
178.7
176.9
180.0
95.0
150.4
160.8
162.4
157.1
42.7
179.7
179.9
102.6
HOH...S(CH 3 ) 2 (47)
-3.56
-1.23
2.33
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.32
-3.76
2.46
-1.10
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-0.46
-1.54
-2.95
-1.25
0.50
0.73
8.99
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-3.53
-16.58
7.16
-1.10
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.99
0.43
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-3.91
-3.16
-1.44
-17.49
-5.50
0.96
-0.08
1.68
1.81
12.98
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-13.21
-2.40
-3.20
3.74
14.58
16.39
OHH...(-)O2 CCH3 , bidentate (66)
-21.85
-22.84
-0.99
a
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.77
2.78
3.40
3.40
3.41
3.49
3.49
4.56
3.51
3.04
3.05
3.43
3.82
3.50
2.84
2.80
2.97
2.81
3.09
3.29
2.81
3.20
3.53
2.86
3.11
3.24
3.24
2.69
2.69
0.29
0.29
0.03
-0.10
-0.10
-0.01
-0.64
-0.43
0.42
0.53
1.19
1.01
0.21
0.15
0.31
0.10
-0.25
0.29
0.11
0.34
0.68
0.16
0.41
0.40
0.40
-0.07
-0.08
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
2.06
2.08
3.60
2.46
2.48
3.75
2.79
3.99
3.13
2.09
2.09
2.84
4.26
3.85
1.80
2.03
2.08
1.84
2.12
2.27
1.76
3.48
3.76
1.82
2.08
2.24
2.24
1.81
1.81
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
142.9
141.8
70.4
166.0
162.6
66.7
129.3
120.4
94.8
171.7
176.2
116.9
57.4
62.2
174.1
135.8
151.5
175.5
178.1
177.7
177.2
65.9
69.1
175.5
179.3
162.5
162.5
147.2
147.2
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-VI. _________________________________________________________________________________
MSI_CHARMm vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.83
-6.75
-0.36
-1.73
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.24
-5.19
-6.49
-4.59
-5.66
-6.75
-6.25
-5.06
-3.36
-3.56
-0.14
0.96
-0.39
1.25
2.44
-1.57
1.93
0.10
0.64
13.54
H3 CCOOH...OHH (13)
-10.94
-6.30
4.64
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-4.15
7.08
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-7.25
-2.35
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-6.61
-2.79
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.79
-7.47
-5.68
-5.59
0.41
-1.08
-1.86
0.22
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.76
2.76
2.76
2.87
2.97
2.77
2.93
2.98
2.87
2.95
2.87
3.25
2.89
2.89
3.22
2.82
3.16
2.74
2.94
2.80
2.84
2.91
2.90
2.90
2.96
2.88
0.02
0.18
0.18
0.16
0.25
0.06
0.22
0.31
0.08
0.29
0.08
0.46
0.32
0.32
0.64
0.21
0.62
0.12
-0.03
-0.15
-0.06
-0.30
0.17
0.14
0.19
0.16
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
1.78
3.21
1.99
2.02
1.84
2.10
2.03
2.00
1.99
2.15
2.78
1.94
1.94
2.40
1.99
2.21
1.96
2.05
2.70
2.07
2.09
2.13
1.97
2.06
2.02
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
173.3
177.5
53.9
151.9
171.7
163.0
142.7
179.5
150.2
179.1
130.4
110.9
170.4
170.4
144.0
143.4
174.9
135.6
154.5
85.9
136.2
141.9
135.7
162.0
154.8
148.0
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-6.18
-5.20
-6.87
-11.68
0.70
0.77
1.16
3.11
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-8.38
-7.83
-8.08
-0.26
-0.13
-4.22
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-6.81
-5.39
-8.21
-8.21
-5.60
1.09
0.66
0.00
-4.11
-2.09
H2 NH...NH3 , linear Cs (33)
-3.38
-4.52
-1.14
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.39
-2.43
-10.83
-7.42
-5.31
-8.75
-4.56
-3.14
0.82
4.65
-3.83
0.35
1.01
-2.85
2.08
7.90
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-2.94
-8.93
3.81
-0.97
Vinylamine...OH2 (44)
-3.80
-3.89
-0.09
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.91
3.11
2.90
2.91
2.91
2.85
2.82
3.39
3.39
2.96
3.08
2.90
2.90
2.75
2.75
2.75
2.75
2.96
3.15
2.94
2.81
3.04
2.97
2.99
3.06
3.26
3.15
2.96
2.97
3.01
0.17
0.25
0.20
0.15
0.15
0.05
-0.01
-0.26
-0.28
0.26
0.24
0.28
0.09
-0.26
-0.26
-0.40
-0.40
0.16
0.36
0.15
0.08
0.24
0.15
0.22
0.24
0.56
0.39
0.08
0.21
-0.03
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.98
2.11
1.99
1.90
1.90
1.95
1.97
3.55
3.55
2.01
2.08
2.08
3.46
2.03
2.03
2.03
2.03
2.02
2.26
1.96
2.32
2.07
1.98
2.31
2.22
2.59
2.38
2.03
3.60
3.45
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
161.1
179.3
158.0
176.2
176.2
147.1
140.6
72.8
72.8
173.0
177.0
143.6
48.2
125.8
125.8
125.8
125.8
162.9
155.6
176.0
111.4
168.9
180.0
127.1
139.1
126.8
136.8
151.7
43.1
56.3
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.17
-2.96
-1.68
0.45
-0.03
1.87
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.20
-4.61
2.59
-1.95
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-5.63
-1.39
-2.31
-5.56
-3.43
-0.43
-0.04
6.37
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH (55)
-10.69
-15.48
-11.75
-12.82
-1.06
2.66
Methylethylhydroxylamine...OH2 (56)
-7.41
-8.95
-1.54
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-3.52
-2.72
-3.51
-20.25
-20.18
1.35
0.37
-0.39
-0.95
-1.70
Imidazolium...OH2 (62)
OHH...(-)O2 CCH3 , bidentate (66)
-16.95
-21.85
-17.18
-17.23
-0.23
4.62
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.77
2.78
3.01
3.08
3.24
3.24
3.42
3.21
3.21
3.30
3.22
3.15
2.95
2.86
2.78
2.84
2.76
2.74
3.10
3.08
3.55
3.02
2.76
2.88
2.88
2.88
2.93
2.93
0.07
-0.25
0.13
0.13
0.04
-0.39
-0.39
-1.26
-0.93
-0.32
0.33
-0.03
0.15
0.36
0.12
0.08
0.44
0.37
0.21
0.02
0.06
0.03
0.03
0.18
0.16
0.15
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
2.06
2.08
2.41
2.34
2.77
2.78
3.19
3.13
2.38
2.45
2.48
2.36
2.08
1.89
1.96
1.97
1.96
2.99
3.20
2.23
2.72
2.01
1.88
1.97
1.97
1.94
2.11
2.11
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
142.9
141.8
117.7
111.0
111.2
110.7
95.4
86.2
143.2
146.9
111.7
139.1
151.5
157.9
141.9
148.0
130.4
65.7
75.0
146.4
145.4
178.4
140.5
148.1
148.1
159.0
140.6
140.6
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-VII. ________________________________________________________________________________
CHARMM 22a vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)b
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.83
-5.21
-0.36
-0.19
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-17.10
-7.06
-6.64
-6.99
-6.50
-8.08
-5.34
-14.06
-0.96
-0.49
-0.90
-0.66
0.03
-0.16
3.04
H3 CCOOH...OHH (13)
-10.94
-10.16
0.77
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-5.97
-8.03
-14.78
-6.16
-8.37
-12.65
-0.19
-0.34
2.13
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.67
-8.06
-6.28
0.45
-0.36
-2.42
H2 NH...HNH2 , cyclic C2h (32)
-3.51
-3.29
0.22
H2 NH...NH3 , linear Cs (33)
-3.38
-3.60
-0.22
HOH...NH3 (34)
-7.22
-6.67
0.54
2.73
2.58
2.
MMFF VII. Characterization of MMFF94, MMFF94s, and Other Widely Available
Force Fields for Conformational Energies and for Intermolecular-Interaction
Energies and Geometries.
THOMAS A. HALGREN
Molecular Systems, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065
Contents:
Comparisons of ab initio "MP4SDQ/TZP" and calculated force-field results for 147 conformational energies:
• Table SM-I
Detailed comparisons of calculated force-field intermolecular interaction energies and geometries to scaled quantum mechanical results:
• MMFF94 (Table SM-II)
• MMFF94s (Table SM-III)
• CFF95 (Table SM-IV)
• CVFF (Table SM-V)
• MSI CHARMm (Table SM-VI)
• CHARMM 22 (Table SM-VII)
• AMBER* (Table SM-VIII)
• OPLS* (Table SM-IX)
• MM2* (Table SM-X)
• MM3* (Table SM-XI)
TABLE SM-I. ________________________________________________________________________________________
Comparison of Ab Initio "MP4SDQ/TZP" and Empirical Force Field Conformational Energies (kcal/mol)
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
1.03
1.90
0.41
1.09
1.97
0.44
1.28
2.18
0.40
1.83
3.09
0.95
3.44#
2.46
2.68#
1.57
2.33
0.37
0.41
1.98
-0.98
alanine dipeptide analog, α'- C7eq
0.91
1.08
2.20
4.88
1.08
1.11
1.58
5.24
1.14
1.12
1.83
4.85
-0.16
0.76
1.43
4.54
2.13
2.58#
1.43
7.04#
1.29
1.68
1.72
6.22
0.37
1.69
2.98
4.32
5.24##
5.52##
1.36
---
0.65
0.00
1.16
3.60
alanine dipeptide analog, β2' - C7eq
2.76
---
2.47
---
---
---
1.84
---
---
alanine dipeptide analog, αL - C7eq
N-OH,N-methylacetamide,
o-n-c=o cis - trans
N-OH,N-Et acetamide,
[o-n-c=o trans, c-c-n-o g] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH,N-Et acetamide,
[o-n-c=o trans, c-c-n-o trans] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH,N-Et acetamide,
[o-n-c=o cis, c-c-n-c(=o) sk] [o-n-c=o cis, c-c-n-c(=o) g]
N-OH, N-Me propionamide,
[o-n-c=o trans, c-c-c=o cis] [o-n-c=o cis, c-c-c=o cis]
4.10
4.28
3.87
---
---
---
---
---
1.16#
0.04
-0.19
0.01
1.95#
---
---
0.24
0.53
0.14
-1.97#
2.55#
---
---
1.50
---
1.56
-2.39##
---
---
9.32##
---
---
0.08
---
0.27
---
0.04
---
---
---
---
0.04
0.24
0.08
-2.21#
5.17##
9.46##
---
---
Conformational comparison
Amides:
N-methylformamide, cis - trans
N-methylactamide, cis - trans
N-formylformamide,
o=c-n-h cis,trans - cis,cis
glycine dipeptide analog, C5 - C7
alanine dipeptide analog, C5 - C7eq
alanine dipeptide analog, C7ax - C7eq
OPLS*
-5.40## -5.03## -9.38##
3.82##
4.81## 10.08##
MM2*
MM3*
0.46
1.74
-1.10#
1.50
2.31
1.72
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
0.96
1.24
1.07
0.72
1.24
1.09
0.26
0.26
---
alanine dipeptide, α' - C7eq
1.66
1.64
2.20
5.35
1.40
1.42
1.84
5.66
1.62
1.68
2.26
5.47
1.08
1.79
1.17
5.34
2.55
2.93
1.84
7.30#
alanine dipeptide, β2 - C7eq
3.20
---
3.06
---
alanine dipeptide, αL - C7eq
4.25
4.74
4.75
4.79
5.86
0.85
0.35
4.89
5.87
0.84
1.91#
1.64
0.21
2.22
1.65
Conformational comparison
N-OH, N-Me propionamide,
[o-n-c=o trans, c-c-c=o sk] [o-n-c=o cis, c-c-c=o cis]
N-OH, N-Me propionamide,
[o-n-c=o cis, c-c-c=o sk] [o-n-c=o cis, c-c-c=o cis]
glycine dipeptide, C5 - C7
alanine dipeptide, C5 - C7eq
alanine dipeptide, C7ax - C7eq
Carboxylic Acids:
formic acid, trans - cis
acetic acid, trans - cis
propanoic acid, c-c-c=o sk - cis
gyloxylic acid,
[o=c-c=o trans, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
glycolic acid, o=c-c-o sk - cis
propenoic acid, c=c-c=o trans - cis
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,cis] [o=c-c=o trans, o=c-o-h trans,trans]
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,trans] [o=c-c=o trans, o=c-o-h trans,trans]
-2.41##
3.42#
AMBER*
OPLS*
MM3*
---
---
2.19
---
---
-1.20#
-0.69#
2.19
---
-0.70#
0.44
2.95
5.48
5.65##
6.05##
1.53
---
1.25
0.56
1.34
4.26
---
---
---
---
---
---
---
---
---
---
---
4.89
5.87
0.84
1.91#
4.48
6.05
0.90
2.94#
5.97
4.76
0.80
0.89
6.55#
7.23
-0.22
1.07
0.80
0.25
0.97
0.80
0.25
0.97
2.57
-2.76## -0.71#
0.70
-0.39
-0.03
6.22## 7.46## 0.01#
1.90
1.90
3.94##
4.05##
5.17## 11.29##
MM2*
1.34
7.64# 11.38## 4.89
6.67
13.66## 5.70
-0.10
0.52
0.71
5.08## -5.68## -0.49
-3.50## 0.94
2.88
-0.14
-0.05
-1.17
9.84## -8.85## -1.74##
6.30## -2.61## -0.34#
Conformational comparison
pyruvic acid,
[o=c-c=o cis, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
Esters:
methyl formate, o=c-o-c trans - cis
methyl acetate, o=c-o-c trans - cis
vinyl formate, c=c-o-c cis - trans
ethyl formate, c-o-c-c g - a
isopropyl formate, c-c-o-c g,g - g,a
phenyl acetate, o=c-o-c cis - trans
methyl glycolate, o=c-c-o sk - cis
Congujated systems:
1,3-butadiene, g - s-trans
2-methyl-1,3-butadiene, g - s-trans
2-methyl-but-1-ene-3-one,
c=c-c=o cis - trans
2-methylpropenamide, c=c-c=o cis - sk
propenamide, c=c-c=o sk - cis
but-1-ene-3-one, c=c-c=o cis - trans
acrolein, c=c-c=o cis - trans
2-methylpropenal, c=c-c=o cis - trans
2-methylpropenoic acid,
c=c-c=o cis - trans
1,3-pentadiene,
[c=c-c=c g, c-c=c-c trans] [c=c-c=c s-trans, c-c=c-c trans]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
1.67
2.42
2.42
2.97
2.48
1.52
5.65
8.21
2.79
0.34
2.43
4.30
1.48
5.28
8.27
2.83
0.44
2.43
4.50
2.43
5.28
8.27
2.83
0.44
2.43
4.50
2.43
5.09
8.67
--0.67
2.16
2.58#
2.40
2.39
2.20
2.08
2.46
2.12
1.90
2.46
2.12
1.90
3.39
2.79
-0.42#
1.05
0.61
0.43
2.03
3.14
0.60
1.04
0.57
0.28
2.05
3.15
0.62
1.00
0.60
0.28
2.05
3.15
0.62
-0.42
6.08## -3.13## 0.16
0.31
-3.02## -1.77# -2.26#
0.69
0.58
0.67
1.43
1.59
2.47
2.03
1.69
-0.07## 5.50#
1.40#
0.64#
-0.45
0.71
-0.52
0.38
2.43
2.46
2.46
3.24
5.54
9.09
4.79#
--5.58##
1.32#
-3.25##
2.39
1.95
2.46
2.56
OPLS*
4.42#
1.34## 0.87##
7.42
7.47
----0.99
0.69
2.65
2.84
2.06#
4.93
0.35
-0.03#
2.45
3.29
-0.57#
2.70
2.80
1.85
1.37
3.19
MM2*
MM3*
-4.13## -0.16#
5.61
6.68#
2.84
0.27
0.74#
8.80##
2.22
2.18##
7.85
--0.23
1.60
1.28##
2.84
2.74
2.49
1.66
1.72
1.63
1.95
2.90#
-0.84
0.50
1.64
3.25
-1.18#
1.04
-0.79
0.71
1.98
3.46
1.30
2.83
1.83
Conformational comparison
1,3-pentadiene,
[s-trans, c-c=c-c cis] [s-trans, c-c=c-c trans]
Aldehydes and ketones:
propionaldehyde, c-c-c=o sk - cis
2-butanone c-c-c=o sk - cis
methyl ispropyl ketone,
o=c-c(ch3)2-h cis - trans
butyraldehyde, c-c-c-c g - a
but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk+, c-c-c=o sk+]
but-3-enal,
[c=c-c-c sk-, c-c-c=o sk+] [c=c-c-c sk+, c-c-c=o sk+]
3-methyl-but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk, c-c-c=o sk]
isobutyraldehyde, h-c(=0)-c-h a - g
2-formylpropanal, o-c-c-c(=o) a - g
4-oxobutanal (o=c-c-c, c-c-c=o cis, cis),
c-c-c-c s-trans - g
2,3-butanedione, c-c-c-c g - s-trans
Halides:
1,2-difluoroethane, a - g
1,2-dicloroethane, g - a
1-fluoropropane, a - g
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
1.27
2.11
2.11
2.15
0.70
1.29
1.97
2.23
1.12
0.83
0.98
0.69
0.53
0.83
0.89
0.53
0.83
0.89
1.09
1.35
1.24
0.32
0.19
0.87
1.65
1.73
1.65
-0.46
-0.04
0.40
0.90
1.57
1.36
1.10
1.61
1.53
0.14
0.20
0.11
-0.05
0.11
-0.05
0.87
---
0.89
1.16
1.27
-0.96
1.08
-0.11
0.84
0.95
0.91
2.11#
0.29
0.98
0.98
0.65
0.71
0.51
0.62
0.07
0.51
0.43
0.72
0.72
0.06
1.34
0.08
1.31
1.25
2.68#
0.37
0.18
0.70
0.56
0.14
0.77
0.56
0.14
0.77
0.97
0.01
-1.34#
-0.49
-1.94#
0.03
0.99
0.25
-0.24
1.16
-0.33
-1.37#
5.40
---
---
3.51#
4.66
---
---
0.58
1.29
0.03
0.63
1.24
0.06
0.63
1.24
0.06
-1.57#
1.22
-0.93
1.05
1.47
-0.12
-1.16#
1.13
0.03
-0.93#
0.87
-0.41
0.04
1.58
-3.85## -2.60#
-0.98#
2.14
7.12#
0.01
1.13
-0.08
2.88#
0.04
1.95
-0.10
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.03
0.00
0.00
1.03
0.15
0.07
0.39
0.23
0.29
2.03
2.03
2.27
1.62
2.08
1.78
4.23#
-0.96#
-0.68#
2.00
2.00
2.12
2.67
3.82#
---
-0.09#
1.03
1.73
1.94
1.94
6.58##
2.63
1.96
1.89
2.60
1.99
1.30
1.81
1.81
1.88
2.37
0.97
1.70
2.27
1.63
2.44
2.11
2.11
2.54
3.37
2.95
1.93
2.99
2.26
0.63
2.25
0.50
2.97
0.50
2.97
0.04
1.96
-0.65
-0.67
-3.98## 2.34
0.41
2.86
0.69
2.84
0.75
2.94
Cations:
N-proplyamine cation, c-c-c-n g - a
ethylguanidine cation, c-c-n=c g - a
0.07
0.62
0.03
0.38
0.03
0.38
0.29
---
-0.32
-1.37#
-0.65
-0.18
0.34
0.33
0.99
0.11
1.12
---
Amines:
propylamine, c-c-c-n g - a
0.33
0.55
0.55
0.00
0.37
-1.08
0.34
0.87
0.87
Conformational comparison
1-chloropropane, g - a
Imines, guanidines, and amidines
formamidine (N puckered),
h-n=c-n cis - trans
N-methylformamidine (N puckered),
n-c=n-c cis - trans
butadiene schiff base,
[c=c-c=n s-cis, h-n=c-c trans] [c=c-c=n s-trans, h-n=c-c cis]
Ketals, acetals, and hemiacetals:
2-methoxytetrahydropyran,
[eq, me-o-c-c a] - [ax, me-o-c-c a]
2,4-dioxapentane,
[c-o-c-o g, o-c-o-c a] [c-o-c-o g+, o-c-o-c g+]
2,5-dimethyl-1,3-dioxane, 5-ax - 5-eq
methoxymethanol,
[c-o-c-o g+, o-c-o-h g-] [c-o-c-o g+, o-c-o-h g+]
-3.12##
Conformational comparison
isopropylamine,
[C1, h-c-n-lp g] [Cs, h-c-n-lp a]
cyclohexylamine, ax - eq
piperidine, n-h ax - eq
N-methylpiperidine, ax - eq
ethylamine, c-c-n-lp a - g
3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
3-aminopropene,
[c=c-c-n sk, c-c-n-lp a] [c=c-c-n sk, c-c-n-lp g]
2-methyl,3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
ethylenediamine,
[n-c-c-n a, c-c-n-lp g+, g+] [n-c-c-n g+, c-c-n-lp g+, g+]
methylethylamine N-oxide, c-n-c-c g - a
methylethylhydroxylamine, c-n-c-c g - a
ethylamine N-oxide, o-n-c-c a - g
ethylhydroxylamine, o-n-c-c a - g
Alcohols:
ethanol, a - g
n-propanol,
[c-c-c-o g-, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.50
0.45
0.45
0.16
-0.07
0.23
0.00
0.15
0.22
0.69
0.78
3.58
0.08
0.50
0.67
0.90
3.28
0.44
0.51
0.67
0.90
3.28
0.44
0.51
0.83
0.05
3.25
0.20
2.44#
1.78
0.13
2.70
0.22
0.00
-0.74
0.14
1.26#
0.26
-0.84
0.62
-0.04
2.32
0.00
-1.07#
1.38
0.31
2.53
0.14
0.71
1.23
0.31
2.31
0.12
1.82
0.15
0.65
0.65
-0.17
-0.21
-0.18
0.68
-0.30
-0.08
0.67
0.61
0.61
1.19
0.47
0.32
-0.93#
1.03
1.75
1.39
1.45
1.45
0.84
1.48
1.20
0.59
1.38
1.69
0.68
0.20
1.41
2.25
0.73
0.05
1.41
2.25
0.73
0.05
-0.73#
1.63
-1.61#
-0.57
3.62#
1.76
1.61
2.98#
0.06
0.23
-0.18
0.58
-0.18
0.58
-0.37
-0.42
-0.23
0.02
12.94## 21.84##
1.23
1.17
0.68
0.55
--1.61
---0.28
--1.20
---0.05
---------
-0.36
-0.76
0.00
0.28
-0.60
0.36
-0.41
0.60
Conformational comparison
n-propanol,
[c-c-c-o g+, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
n-propanol,
[c-c-c-o a, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
n-propanol,
[c-c-c-o g, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
isopropanol, h-c-o-h a - g
cyclopentanol, eq C s - ax C1
cyclopentanol, ax C s- ax C1
cyclopentanol, eq C 1 - ax C1
cyclohexanol, eq Cs - eq C1
cyclohexanol, ax Cs - eq C1
cylohexanol, ax C1 - eq C1
vinyl alcohol, c=c-o-h trans - sk
benzyl alcohol, h-o-c-c a - g
propen-3-ol,
[c=c-c-o sk, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
propen-3-ol,
[c=c-c-o cis, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
2-me-propen-3-ol,
[c=c-c-o c, c-c-o-h a] [c=c-c-o s, c-c-o-h a]
sec-butanol, ga/ga - ga/aga
sec-butanol, ga/gg - ga/ag
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
0.05
0.24
0.24
0.01
-0.43
0.20
-0.17
-0.17
-0.49
0.10
0.12
0.12
0.20
1.11
1.05
1.14
0.18
1.14
0.33
1.43
1.13
1.24
0.17
0.82
0.59
0.47
0.20
1.01
0.32
1.43
1.59
1.10
1.11
OPLS*
MM2*
MM3*
-0.62
0.28
0.36
0.35
-0.16
-0.30
0.00
-0.60
-0.42
-0.23
-0.29
-0.81
0.28
-0.30
-0.06
0.17
0.82
0.59
0.47
0.20
1.01
0.32
1.43
1.59
1.10
0.40
-0.27
-0.33
-0.53#
0.38
-0.49#
0.24
1.58
1.38
0.82
0.02
---0.94#
-0.62#
0.06
0.58
0.40
0.66
2.97#
2.43
0.25
-0.36
--0.70
0.15
-0.87#
-0.57
-0.81#
0.81
1.07
0.00
-0.07
0.00
-0.07
0.00
0.50
0.50
-0.69#
1.23
0.19
0.61
0.40
0.82
-0.23
0.62
1.46
0.58
1.75
1.22
1.20
0.68
0.89
1.35
-0.15
0.77
2.43
0.74
-0.09#
1.33
1.12
1.13
1.13
3.39#
0.49
-0.08
-1.06#
0.83
2.76#
0.38
0.47
0.47
0.94
0.39
-0.71
-1.57#
-0.10
1.53
0.10
0.18
0.33
0.11
0.33
0.11
-0.62
0.23
0.23
-0.32
-0.30
0.05
0.00
0.00
0.07
0.64
0.24
0.69
AMBER*
Conformational comparison
sec-butanol, ag/ag - ga/ag
sec-butanol, ag/ga - ga/ag
sec-butanol, ag/gg - ga/ag
sec-butanol, gg/ag - ga/ag
sec-butanol, gg/ga - ga/ag
sec-butaone, gg/gg - ga/ag
1,2-ethanediol,
[h-o-c-c a, o-c-c-o a, c-c-o-h a] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
1,2-ethanediol,
[h-o-c-c g-, o-c-c-o g+, c-c-o-h g+] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
1,2-ethanediol,
[h-o-c-c g+, o-c-c-o g-, c-c-o-h g+] [h-o-c-c g-, o-c-c-o g+, c-c-o-h a]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
0.48
0.29
0.56
0.75
0.57
1.13
2.71
0.47
0.46
0.59
0.72
0.66
1.14
2.91
0.47
0.46
0.59
0.72
0.66
1.14
2.91
0.57
0.74
1.15
0.87
0.68
0.56
0.70#
1.02
1.06
0.87
0.79
0.43
1.01
2.45
0.93
0.85
1.07
0.40
0.20
0.33
5.69#
0.49
1.15
1.15
1.45
0.79
1.41
1.58
1.58
1.92
1.17
OPLS*
MM2*
MM3*
0.71
0.71
0.71
1.00
1.00
1.00
17.30##
0.53
0.53
1.14
0.82
0.90
1.54
2.30
0.49
0.50
1.14
0.98
0.97
2.06
0.80#
0.29
---
1.47
---
0.37
---
1.50
---
1.74
1.07
1.77
1.48
0.60#
1.49
Ethers:
methyl ethyl ether, g - a
methyl vinyl ether, c=c-o-c skew - cis
diethyl ether,
[c-c-o-c a, c-o-c-c g] [c-c-o-c a, c-o-c-c a]
methoxycyclohexane, eq Cs - ax C1
methoxycyclohexane, eq C1 - ax C1
methyl isopropyl ether, h-c-o-ch3 a - g
1.41
2.27
1.48
1.50
2.22
1.52
1.50
2.22
1.52
2.10
0.01
1.91
1.95
-0.41
1.88
1.95
-0.41
1.88
2.19
0.11
2.10
1.56
-0.70
1.91
2.76
0.34
2.25
2.08
-0.37
2.20
1.53
-0.56
1.73
1.80
-0.76
2.12
Alkanes:
butane, g - a
0.65
0.78
0.78
0.89
0.78
0.39
0.95
0.86
0.81
1.46
-3.10##
1.37
1.53
2.10
1.55
1.79
1.85
-2.90## -3.94##
1.83
1.84
Conformational comparison
cyclohexane, twist-boat - chair
methylcyclohexane, ax - eq
2,3-dimethylbutane, h-c2-c3-h g - a
cyclooctane, D4d crown - Cs boat-chair
cyclooctane,
C2 twist-boat-chair - Cs boat-chair
cyclooctane, S4 - Cs boat-chair
methylcyclobutane, ax - eq
cyclononane, C2 [144] - D3 [333]
cyclononane, C2 [225] - D3 [333]
cyclononane, C1 [234] - D3 [333]
Alkenes:
1-butene, c=c-c-c cis - sk
1-pentene (c=c-c-c skew),
c-c-c-c g - a
2-methyl-1-butene, c=c-c-c skew - cis
1,4-pentadiene,
c=c-c-c sk+,sk- - sk-,sk2-butene, cis - trans
2-pentene,
[c-c=c-c cis, c-c-c=c sk] [c-c=c-c trans, c-c-c=c sk]
Thiols, sulfides, and disulfides:
ethanethiol, c-c-s-h a - g
ethyl methyl disulfide, c-c-s-s a - g
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
6.14
1.69
0.04
2.00
1.71
5.93
1.37
-0.23
1.44
1.99
5.93
1.37
-0.23
1.44
1.99
7.08
1.84
0.13
1.21
2.30
6.72
1.80
0.40
0.45#
1.88
2.97
0.77
1.97
0.99
3.65
3.27
0.78
1.41
1.21
3.81
3.27
0.78
1.41
1.21
3.81
0.16#
1.21
1.02
-1.63#
2.03#
4.48#
0.06
0.37#
1.12
3.45
0.26
0.61
0.26
0.51
0.26
0.51
0.72
0.90
0.46
-0.10
0.66
0.11
0.02
0.33
-0.03
0.43
-0.03
0.43
-0.07
0.33
-0.93
0.19
1.27
1.31
1.35
1.33
1.35
1.33
1.43
1.35
0.74
0.76
0.68
0.76
0.68
0.76
0.33
-0.31
OPLS*
MM2*
MM3*
5.79
0.90
-0.22
0.83
1.77
6.77
1.78
-0.48
-1.67##
1.20
5.36
1.78
0.15
0.96
1.66
5.76
1.77
0.38
1.12
1.85
3.63
0.17
0.53
1.07
3.66
6.51##
0.63
-1.02#
0.80
4.31
3.12
0.58
0.77
0.75
3.16
2.62
0.92
1.15
0.84
3.04
1.00
0.60
0.49
0.78
0.68
0.42
-0.97
0.44
-0.98
0.25
-0.06
0.07
-0.38
0.27
1.61
1.61
1.55
1.43
2.49
2.39
1.43
1.29
1.02
0.99
-0.78#
0.11
-0.20
-1.29#
0.00
0.04
0.28
-0.19
-0.04
0.05
AMBER*
Conformational comparison
1-propanethiol,
[s-c-c-c g-, h-s-c-c g+] [s-c-c-c a, h-s-c-c g]
1-propanethiol,
[s-c-c-c g, h-s-c-c a] [s-c-c-c a, h-s-c-c g]
1,2-ethanedithiol,
[all anti] [h-s-c-c a,g+, s-c-c-s g-]
1,2-ethanedithiol,
[h-s-c-c a,a, s-c-c-s g] [h-s-c-c a,g+, s-c-c-s g-]
methyl propyl sulfide,
[c-s-c-c g-, s-c-c-c g-] [c-s-c-c g, s-c-c-c a]
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c g] [c-s-c-c g, s-c-c-c a]
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c a] [c-s-c-c g, s-c-c-c a]
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
0.30
0.37
0.37
1.59
-0.84
1.51
0.48
0.84
1.04
1.23
0.95
0.95
2.26
-1.65#
1.53
0.48
0.92
0.65
0.86
1.17
1.17
0.15
-0.95#
6.92##
5.17#
-0.92#
-1.71#
1.77
2.24
2.24
1.71
0.26#
1.62
5.51##
0.68
0.34
0.09
0.05
0.05
1.56
-0.08
1.21
0.12
0.58
0.61
0.66
0.60
0.60
-0.03
0.18
0.94
-0.24
0.24
0.51
0.25
0.33
0.33
-1.66#
0.23
-0.24
-0.43
-0.39
-0.18
a For
the OH14 conformers (sec-butanol), in the conformational designations "wx/yz", "w" indicates the conformation of the c-c-c-o
angle, "x" that of the c-c-c-c angle,"y" that of the h-o-c-ch2 angle, and "z" that of the h-o-c-ch3 angle.
# Denotes a conformational enregy that differs from the reference "MP4SDQ/TZP" value by > 1.5 kcal/mol.
## Denotes a conformational enregy that differs from the reference "MP4SDQ/TZP" value by > 3 kcal/mol.
TABLE SM-II. _________________________________________________________________________________
MMFF94 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.61
-4.91
-0.14
0.11
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.33
-6.15
-6.04
-5.98
-8.45
-5.08
-8.48
-5.46
-3.78
-17.09
-0.23
0.00
0.05
-0.14
-0.35
0.10
-0.30
-0.30
0.22
0.01
H3 CCOOH...OHH (13)
-10.94
-11.70
-0.76
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-6.10
-1.20
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.80
-6.84
-2.62
-6.74
0.40
-0.45
1.20
-0.93
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.75
2.78
2.78
2.73
2.75
2.73
2.77
2.69
2.83
2.68
2.81
2.88
2.62
2.62
2.64
2.77
2.61
2.60
2.94
2.79
2.86
3.20
2.87
2.73
2.95
2.71
0.02
0.19
0.19
0.02
0.03
0.02
0.06
0.02
0.04
0.02
0.02
0.10
0.05
0.05
0.07
0.16
0.07
-0.02
-0.04
-0.17
-0.04
-0.01
0.14
-0.03
0.17
0.00
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
2.19
2.19
1.76
1.76
1.74
1.81
1.72
1.89
1.69
1.87
1.97
1.63
1.63
1.67
2.11
1.61
1.92
2.02
2.69
2.02
2.43
1.94
1.75
2.12
1.74
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
170.4
117.0
117.0
168.7
179.9
177.0
166.7
167.5
159.9
176.1
160.4
155.4
169.2
169.2
163.4
122.8
175.4
123.9
155.7
85.4
142.6
135.5
159.0
177.6
142.0
170.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-7.06
-6.86
-8.19
-12.26
-0.19
-0.89
-0.16
2.52
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.69
-9.08
-5.62
0.43
-1.38
-1.76
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-8.07
-6.94
-7.99
-3.95
-3.02
-0.17
-0.89
0.22
0.15
0.49
H2 NH...NH3 , linear Cs (33)
-3.38
-3.67
-0.29
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.83
-6.70
-7.91
-7.93
-6.51
-6.28
-7.10
-10.65
0.39
0.37
-0.91
-0.16
-0.18
-0.39
-0.47
0.38
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-7.95
-7.47
-1.21
0.49
Vinylamine...OH2 (44)
-3.80
-4.61
-0.81
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.71
2.84
2.71
2.81
2.81
2.76
2.76
3.61
3.61
2.71
2.82
2.70
2.85
3.11
3.11
3.03
3.03
2.80
2.82
2.82
2.75
2.86
2.86
2.79
2.97
2.76
2.74
2.90
2.94
2.87
-0.03
-0.03
0.00
0.06
0.06
-0.03
-0.07
-0.05
-0.06
0.00
-0.01
0.08
0.03
0.10
0.10
-0.12
-0.12
0.00
0.02
0.04
0.01
0.05
0.04
0.02
0.15
0.06
-0.02
0.02
0.18
-0.17
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.73
1.82
1.73
1.79
1.79
1.74
1.76
3.49
3.49
1.73
1.80
1.72
1.87
2.40
2.40
2.00
3.36
1.82
1.84
1.81
1.81
1.84
1.84
1.85
2.09
1.80
1.77
1.98
2.11
1.85
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.1
176.9
174.2
173.4
173.4
174.4
165.3
88.5
88.4
174.8
175.4
175.8
175.8
125.4
125.4
178.1
62.7
173.9
173.1
175.6
158.6
179.7
180.0
158.9
142.8
162.0
167.6
148.1
141.1
173.3
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.86
-2.91
-3.48
-0.24
0.02
0.08
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-3.22
-2.71
0.56
-0.05
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-1.25
-2.00
-11.58
-1.25
-0.29
0.27
0.36
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-10.61
-14.87
0.08
0.61
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-4.48
-2.84
-3.43
-21.17
-19.02
0.39
0.25
-0.31
-1.87
-0.54
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-17.60
-18.75
-19.71
-0.65
-1.77
-0.12
Formaldehydeiminium...OH2 (65)
OHH...(-)O2 CCH3 , bidentate (66)
-19.98
-21.85
-21.65
-22.62
-1.67
-0.77
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.66
2.77
2.78
2.87
3.38
3.35
3.35
3.55
3.69
3.69
4.37
4.02
3.49
2.66
3.02
2.64
2.59
2.74
2.79
2.88
2.66
3.35
3.00
2.62
2.78
2.78
2.62
2.61
2.78
2.78
2.65
2.74
2.74
-0.06
0.05
0.23
0.23
0.17
0.10
0.10
-0.19
-0.13
0.02
0.03
0.12
0.01
0.10
0.11
0.13
0.22
-0.04
0.01
0.00
-0.08
-0.07
-0.07
-0.08
-0.10
-0.05
-0.05
-0.01
-0.03
-0.03
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
1.78
2.06
2.08
1.85
2.03
2.38
3.62
2.58
3.03
3.34
3.55
2.70
2.55
1.66
2.43
1.65
1.66
2.10
1.94
2.10
1.69
2.45
1.97
1.57
1.87
1.87
1.59
1.57
1.89
1.89
1.61
1.87
1.87
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
163.4
142.9
141.8
172.8
172.8
170.8
66.4
174.6
126.8
103.6
144.2
167.3
163.2
174.3
115.2
178.6
154.6
117.6
143.2
135.1
172.7
153.9
173.9
176.7
146.8
146.8
173.4
177.2
143.6
143.6
176.6
145.7
145.7
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-III. _________________________________________________________________________________
MMFF94s vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.61
-4.91
-0.14
0.11
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.33
-6.15
-6.04
-5.98
-8.45
-5.08
-8.48
-5.46
-3.78
-17.09
-0.23
0.00
0.05
-0.14
-0.35
0.10
-0.30
-0.30
0.22
0.01
H3 CCOOH...OHH (13)
-10.94
-11.70
-0.76
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-6.10
-1.20
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.80
-6.84
-2.62
-6.74
0.40
-0.45
1.20
-0.93
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.75
2.78
2.78
2.73
2.75
2.73
2.77
2.69
2.83
2.68
2.81
2.88
2.62
2.62
2.64
2.77
2.61
2.60
2.94
2.79
2.86
3.20
2.87
2.73
2.95
2.71
0.02
0.19
0.19
0.02
0.03
0.02
0.06
0.02
0.04
0.02
0.02
0.10
0.05
0.05
0.07
0.16
0.07
-0.02
-0.04
-0.17
-0.04
-0.01
0.14
-0.03
0.17
0.00
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
2.19
2.19
1.76
1.76
1.74
1.81
1.72
1.89
1.69
1.87
1.97
1.63
1.63
1.67
2.11
1.61
1.92
2.02
2.69
2.02
2.43
1.94
1.75
2.12
1.74
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
170.4
117.0
117.0
168.7
179.9
177.0
166.7
167.5
159.9
176.1
160.4
155.4
169.2
169.2
163.4
122.8
175.4
123.9
155.7
85.4
142.6
135.5
159.0
177.6
142.0
170.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-7.06
-6.87
-8.25
-12.26
-0.19
-0.90
-0.22
2.52
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.69
-9.06
-5.33
0.43
-1.36
-1.47
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-8.14
-6.90
-8.30
-4.26
-3.02
-0.24
-0.85
-0.09
-0.16
0.49
H2 NH...NH3 , linear Cs (33)
-3.38
-3.67
-0.29
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.83
-6.70
-7.91
-7.93
-6.51
-6.28
-7.10
-10.68
0.39
0.37
-0.91
-0.16
-0.18
-0.39
-0.47
0.35
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-7.95
-7.02
-1.21
0.94
Vinylamine...OH2 (44)
-3.80
-4.23
-0.43
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.71
2.84
2.70
2.81
2.81
2.76
2.76
3.64
3.64
2.71
2.83
2.70
2.84
3.11
3.11
3.03
3.03
2.80
2.82
2.82
2.75
2.86
2.86
2.79
2.97
2.77
2.74
2.88
3.22
2.88
-0.03
-0.03
0.00
0.06
0.06
-0.03
-0.07
-0.01
-0.02
0.00
-0.01
0.08
0.03
0.10
0.10
-0.12
-0.12
0.00
0.02
0.04
0.01
0.05
0.04
0.02
0.16
0.07
-0.02
0.00
0.46
-0.16
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.73
1.81
1.72
1.79
1.79
1.74
1.75
3.54
3.54
1.73
1.80
1.72
1.87
2.40
2.40
2.00
3.36
1.82
1.84
1.81
1.81
1.84
1.84
1.85
2.13
1.80
1.77
1.88
3.84
1.85
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.1
179.9
174.3
173.4
173.4
174.1
166.8
88.0
88.0
174.9
175.5
177.0
178.2
125.4
125.4
178.1
62.7
173.9
173.1
175.6
158.6
179.7
180.0
158.9
137.8
167.5
167.6
165.7
45.0
176.9
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.54
-2.91
-3.48
0.08
0.02
0.08
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-3.22
-2.71
0.56
-0.05
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-1.25
-2.00
-11.58
-1.25
-0.29
0.27
0.36
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH (55)
-10.69
-15.48
-10.61
-14.87
0.08
0.61
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-4.48
-2.84
-3.43
-21.17
-19.02
0.39
0.25
-0.31
-1.87
-0.54
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-17.60
-18.75
-19.71
-0.65
-1.77
-0.12
Formaldehydeiminium...OH2 (65)
OHH...(-)O2 CCH3 , bidentate (66)
-19.98
-21.85
-21.65
-22.62
-1.67
-0.77
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.66
2.77
2.78
2.88
3.38
3.35
3.35
3.55
3.69
3.69
4.37
4.02
3.49
2.66
3.02
2.64
2.59
2.74
2.79
2.88
2.66
3.35
3.00
2.62
2.78
2.78
2.62
2.61
2.78
2.78
2.65
2.74
2.74
-0.06
0.05
0.23
0.23
0.17
0.10
0.10
-0.19
-0.13
0.02
0.03
0.12
0.01
0.10
0.11
0.13
0.22
-0.04
0.01
0.00
-0.08
-0.07
-0.07
-0.08
-0.10
-0.05
-0.05
-0.01
-0.03
-0.03
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
1.78
2.06
2.08
1.86
2.03
2.38
3.62
2.58
3.03
3.34
3.55
2.70
2.55
1.66
2.43
1.65
1.66
2.10
1.94
2.10
1.69
2.45
1.97
1.57
1.87
1.87
1.59
1.57
1.89
1.89
1.61
1.87
1.87
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
163.4
142.9
141.8
174.9
172.8
170.8
66.4
174.6
126.8
103.6
144.2
167.3
163.2
174.3
115.2
178.6
154.6
117.6
143.2
135.1
172.7
153.9
173.9
176.7
146.8
146.8
173.4
177.2
143.6
143.6
176.6
145.7
145.7
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-IV. _________________________________________________________________________________
CFF95 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-5.40
-4.26
1.07
0.76
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-4.61
-6.53
-5.65
-2.93
-6.28
-3.97
-6.32
-5.37
-3.86
-10.57
1.49
-0.38
0.44
2.91
1.82
1.21
1.86
-0.21
0.14
6.53
H3 CCOOH...OHH (13)
-10.94
-9.00
1.94
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-8.97
2.26
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.20
0.70
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-3.82
0.00
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-3.78
-4.58
-4.58
-3.85
1.42
1.81
-0.76
1.96
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.90
2.88
2.88
2.93
2.84
2.86
3.08
2.88
3.03
2.85
2.90
3.14
2.88
2.88
2.80
3.03
2.80
2.88
3.16
3.03
3.05
3.22
3.03
2.98
4.30
2.98
0.17
0.30
0.30
0.22
0.11
0.15
0.37
0.21
0.24
0.19
0.12
0.36
0.31
0.31
0.22
0.42
0.26
0.27
0.19
0.07
0.15
0.01
0.30
0.22
1.52
0.27
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.93
2.25
2.25
1.97
1.86
1.89
2.11
1.91
2.10
1.87
1.96
2.22
1.91
1.91
1.83
2.48
1.84
2.29
2.21
2.78
2.27
2.42
2.09
2.00
3.49
2.03
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
169.6
121.4
121.4
168.1
179.0
179.0
176.3
173.8
159.3
179.3
162.1
156.6
169.0
169.0
168.3
115.5
167.3
118.3
163.8
95.3
136.5
139.4
160.8
179.2
141.3
166.8
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-4.13
-7.41
-5.67
-10.02
2.74
-1.44
2.36
4.76
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-6.49
-7.88
-5.28
1.63
-0.18
-1.42
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-5.66
-7.43
-7.50
-8.29
-1.29
2.23
-1.38
0.71
-4.19
2.22
H2 NH...NH3 , linear Cs (33)
-3.38
-1.38
2.00
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-3.75
-3.58
-7.81
-6.05
-6.82
-6.28
-4.25
-8.51
3.47
3.50
-0.81
1.72
-0.49
-0.39
2.38
2.52
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.91
-7.00
0.83
0.96
Vinylamine...OH2 (44)
-3.80
-4.33
-0.53
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.99
2.91
2.95
2.99
2.99
2.98
2.95
3.84
3.84
2.95
2.90
2.82
2.82
3.16
3.16
3.20
3.20
2.97
3.04
2.85
3.14
2.88
2.89
3.20
2.98
2.90
2.90
3.01
2.97
2.98
0.25
0.04
0.25
0.23
0.23
0.19
0.12
0.19
0.17
0.24
0.06
0.20
0.01
0.15
0.15
0.05
0.05
0.18
0.24
0.06
0.41
0.07
0.07
0.42
0.17
0.20
0.14
0.13
0.20
-0.06
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
2.01
1.89
1.98
1.97
1.97
2.06
1.95
3.69
3.69
1.98
1.88
1.88
3.49
2.42
2.42
2.19
3.25
2.00
2.08
1.82
2.25
1.84
1.85
2.32
2.11
1.92
1.92
2.10
2.06
1.97
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
179.9
179.1
172.2
177.5
177.5
149.8
167.4
91.1
91.1
172.1
177.0
160.3
40.3
130.0
130.0
177.7
78.4
173.6
169.3
178.0
150.0
175.7
180.0
148.8
142.5
171.2
179.6
148.2
152.8
177.0
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-5.17
-2.19
-2.05
-0.55
0.74
1.51
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.71
-4.36
2.07
-1.70
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-4.38
-1.23
-2.75
-6.04
-2.18
-0.26
-0.48
5.90
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-7.20
-21.09
3.49
-5.60
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.51
0.90
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-1.69
-1.09
-1.18
-18.81
-16.40
3.17
1.99
1.94
0.49
2.08
Imidazolium...OH2 (62)
OHH...(-)O2 CCH3 , bidentate (66)
-16.95
-21.85
-15.95
-17.22
1.00
4.63
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.77
2.78
2.93
3.58
3.28
3.28
3.47
3.63
3.63
4.40
3.77
3.09
2.86
3.27
2.87
3.45
2.73
2.84
3.58
3.09
4.43
3.36
2.74
2.96
2.96
2.78
2.86
2.86
-0.01
0.25
0.16
0.16
0.09
0.04
0.04
-0.16
-0.38
-0.38
0.23
0.37
0.24
0.96
0.09
0.18
0.92
0.39
1.10
0.36
0.04
0.11
0.11
0.07
0.09
0.08
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
2.06
2.08
1.91
2.84
2.30
3.64
2.50
3.57
2.91
3.77
3.02
2.13
1.88
2.74
1.89
3.83
1.72
1.87
3.99
2.13
3.81
2.35
1.74
2.02
2.02
1.74
2.00
2.00
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
142.9
141.8
175.0
113.4
178.2
60.6
172.9
85.7
131.4
125.0
114.4
167.5
177.6
112.8
177.3
59.9
170.5
173.0
58.3
169.7
125.0
179.8
167.9
152.4
152.4
172.4
143.9
143.9
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-IV. _________________________________________________________________________________
CVFF vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.40
-4.74
0.07
0.28
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-4.41
-6.78
-5.03
-5.09
-7.57
-4.18
-7.33
-4.31
-3.87
-11.14
1.69
-0.63
1.06
0.75
0.53
1.00
0.85
0.85
0.13
5.96
H3 CCOOH...OHH (13)
-10.94
-8.82
2.12
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.31
1.92
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.24
0.66
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.31
-5.49
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.85
-6.19
-3.20
-6.01
0.36
0.20
0.62
-0.20
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.76
2.81
2.81
2.81
2.66
2.69
2.79
2.67
2.83
2.66
2.81
2.93
2.66
2.66
2.66
3.00
2.65
2.74
3.52
2.80
2.74
4.83
2.79
2.75
4.04
2.75
0.03
0.23
0.23
0.09
-0.06
-0.02
0.08
0.01
0.05
0.00
0.02
0.15
0.09
0.09
0.08
0.39
0.11
0.13
0.55
-0.15
-0.16
1.62
0.06
-0.01
1.27
0.03
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.79
2.17
2.17
1.85
1.68
1.72
1.82
1.71
1.88
1.68
1.85
2.01
1.70
1.70
1.70
2.40
1.68
2.05
3.02
1.83
2.05
5.72
1.84
1.77
4.34
1.78
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
173.7
122.3
122.3
168.0
176.0
174.9
173.5
169.3
167.9
177.2
167.5
158.4
171.7
171.7
168.5
119.5
170.4
126.9
113.9
177.7
126.9
21.0
165.6
176.7
65.9
174.5
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-5.30
-4.19
-6.80
-6.53
1.57
1.78
1.23
8.25
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-5.23
-5.69
-4.84
2.89
2.01
-0.98
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-7.18
-4.46
-8.40
-9.06
-0.46
0.72
1.59
-0.19
-4.97
3.05
H2 NH...NH3 , linear Cs (33)
-3.38
-0.50
2.88
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-6.33
-5.89
-6.63
-11.03
-1.99
-4.05
-2.59
-2.28
-3.36
-3.49
5.23
3.02
3.74
3.61
3.27
7.54
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-3.00
-5.74
3.74
2.22
Vinylamine...OH2 (44)
Aniline...OH2 (45)
HSH...OH2 (46)
-3.80
-4.62
-2.93
-1.76
-2.82
-0.98
2.03
1.80
1.95
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.94
3.33
2.76
3.07
2.74
3.00
3.00
3.08
3.02
4.00
4.00
2.73
3.05
2.64
2.65
3.69
3.69
3.69
3.69
3.18
3.07
3.09
3.11
3.48
3.21
3.18
3.17
3.16
3.16
3.15
3.12
3.48
0.02
0.20
0.04
0.24
0.24
0.29
0.19
0.35
0.33
0.02
0.21
0.02
-0.17
0.69
0.69
0.53
0.53
0.39
0.27
0.28
0.29
0.70
0.40
0.48
0.41
0.28
0.40
0.11
0.18
0.15
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
2.20
2.29
1.79
2.04
1.77
1.97
1.97
2.28
2.00
3.82
3.82
1.76
2.02
1.68
3.31
2.92
2.92
2.66
3.80
2.22
2.10
2.06
2.07
3.26
2.28
2.25
2.23
2.19
3.80
2.12
2.09
2.94
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
173.2
175.3
179.2
176.8
175.6
175.9
175.9
133.4
168.8
92.7
92.7
172.1
169.3
168.0
40.6
132.8
132.8
176.0
76.0
173.1
178.7
176.9
180.0
95.0
150.4
160.8
162.4
157.1
42.7
179.7
179.9
102.6
HOH...S(CH 3 ) 2 (47)
-3.56
-1.23
2.33
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.32
-3.76
2.46
-1.10
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-3.45
-0.46
-1.54
-2.95
-1.25
0.50
0.73
8.99
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-3.53
-16.58
7.16
-1.10
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.99
0.43
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-3.91
-3.16
-1.44
-17.49
-5.50
0.96
-0.08
1.68
1.81
12.98
Imidazolium...OH2 (62)
Formamidinium...OH 2 (63)
Formamidinium...OH 2 , cyclic C2v (64)
-16.95
-16.98
-19.59
-13.21
-2.40
-3.20
3.74
14.58
16.39
OHH...(-)O2 CCH3 , bidentate (66)
-21.85
-22.84
-0.99
a
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.71
2.83
2.83
2.77
2.78
3.40
3.40
3.41
3.49
3.49
4.56
3.51
3.04
3.05
3.43
3.82
3.50
2.84
2.80
2.97
2.81
3.09
3.29
2.81
3.20
3.53
2.86
3.11
3.24
3.24
2.69
2.69
0.29
0.29
0.03
-0.10
-0.10
-0.01
-0.64
-0.43
0.42
0.53
1.19
1.01
0.21
0.15
0.31
0.10
-0.25
0.29
0.11
0.34
0.68
0.16
0.41
0.40
0.40
-0.07
-0.08
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
1.91
2.09
2.09
2.06
2.08
3.60
2.46
2.48
3.75
2.79
3.99
3.13
2.09
2.09
2.84
4.26
3.85
1.80
2.03
2.08
1.84
2.12
2.27
1.76
3.48
3.76
1.82
2.08
2.24
2.24
1.81
1.81
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
148.7
142.6
142.6
142.9
141.8
70.4
166.0
162.6
66.7
129.3
120.4
94.8
171.7
176.2
116.9
57.4
62.2
174.1
135.8
151.5
175.5
178.1
177.7
177.2
65.9
69.1
175.5
179.3
162.5
162.5
147.2
147.2
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-VI. _________________________________________________________________________________
MSI_CHARMm vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)a
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.83
-6.75
-0.36
-1.73
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-8.18
-5.16
-4.00
-17.10
-6.24
-5.19
-6.49
-4.59
-5.66
-6.75
-6.25
-5.06
-3.36
-3.56
-0.14
0.96
-0.39
1.25
2.44
-1.57
1.93
0.10
0.64
13.54
H3 CCOOH...OHH (13)
-10.94
-6.30
4.64
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-4.15
7.08
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-7.25
-2.35
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-6.61
-2.79
HOH...skew-Methyl vinyl ether (17)
HOH...Methyl formate (=O) (18)
HOH...Methyl formate (-O-) (19)
HOH...Formaldehyde (20)
-5.20
-6.39
-3.82
-5.81
-4.79
-7.47
-5.68
-5.59
0.41
-1.08
-1.86
0.22
2.73
2.58
2.58
2.72
2.72
2.71
2.71
2.67
2.79
2.65
2.79
2.78
2.57
2.57
2.58
2.61
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.76
2.76
2.76
2.87
2.97
2.77
2.93
2.98
2.87
2.95
2.87
3.25
2.89
2.89
3.22
2.82
3.16
2.74
2.94
2.80
2.84
2.91
2.90
2.90
2.96
2.88
0.02
0.18
0.18
0.16
0.25
0.06
0.22
0.31
0.08
0.29
0.08
0.46
0.32
0.32
0.64
0.21
0.62
0.12
-0.03
-0.15
-0.06
-0.30
0.17
0.14
0.19
0.16
H...Z distance
SQM
FF
2.03
2.31
2.31
2.01
2.01
2.00
2.02
1.95
2.12
1.93
2.11
2.22
1.83
1.83
1.90
2.15
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
1.78
1.78
3.21
1.99
2.02
1.84
2.10
2.03
2.00
1.99
2.15
2.78
1.94
1.94
2.40
1.99
2.21
1.96
2.05
2.70
2.07
2.09
2.13
1.97
2.06
2.02
X–H...Z angle
QM
FF
172.3
111.8
111.8
169.0
174.9
174.6
163.9
174.0
160.8
175.0
163.2
141.6
175.9
175.9
156.3
127.9
171.5
122.2
141.1
151.7
155.0
117.5
155.6
167.0
138.7
147.6
173.3
177.5
53.9
151.9
171.7
163.0
142.7
179.5
150.2
179.1
130.4
110.9
170.4
170.4
144.0
143.4
174.9
135.6
154.5
85.9
136.2
141.9
135.7
162.0
154.8
148.0
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-8.03
-14.78
-6.18
-5.20
-6.87
-11.68
0.70
0.77
1.16
3.11
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-8.38
-7.83
-8.08
-0.26
-0.13
-4.22
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2 NH...HNH2 , cyclic C2h (32)
-7.90
-6.05
-8.21
-4.10
-3.51
-6.81
-5.39
-8.21
-8.21
-5.60
1.09
0.66
0.00
-4.11
-2.09
H2 NH...NH3 , linear Cs (33)
-3.38
-4.52
-1.14
HOH...NH3 (34)
HOH...NH2 CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H 2 O, cyclic (41)
-7.22
-7.07
-7.00
-7.77
-6.33
-5.89
-6.63
-11.03
-6.39
-2.43
-10.83
-7.42
-5.31
-8.75
-4.56
-3.14
0.82
4.65
-3.83
0.35
1.01
-2.85
2.08
7.90
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-2.94
-8.93
3.81
-0.97
Vinylamine...OH2 (44)
-3.80
-3.89
-0.09
2.74
2.87
2.70
2.76
2.76
2.80
2.83
3.65
3.67
2.71
2.84
2.62
2.82
3.01
3.01
3.15
3.15
2.80
2.80
2.79
2.73
2.81
2.82
2.77
2.81
2.70
2.76
2.88
2.77
3.04
2.91
3.11
2.90
2.91
2.91
2.85
2.82
3.39
3.39
2.96
3.08
2.90
2.90
2.75
2.75
2.75
2.75
2.96
3.15
2.94
2.81
3.04
2.97
2.99
3.06
3.26
3.15
2.96
2.97
3.01
0.17
0.25
0.20
0.15
0.15
0.05
-0.01
-0.26
-0.28
0.26
0.24
0.28
0.09
-0.26
-0.26
-0.40
-0.40
0.16
0.36
0.15
0.08
0.24
0.15
0.22
0.24
0.56
0.39
0.08
0.21
-0.03
2.06
2.12
2.00
2.00
2.00
2.09
2.08
3.88
3.88
2.01
2.09
1.94
2.12
2.60
2.61
2.42
3.64
2.09
2.09
2.03
2.10
2.07
2.07
2.12
2.20
2.06
2.11
2.25
2.21
2.19
1.98
2.11
1.99
1.90
1.90
1.95
1.97
3.55
3.55
2.01
2.08
2.08
3.46
2.03
2.03
2.03
2.03
2.02
2.26
1.96
2.32
2.07
1.98
2.31
2.22
2.59
2.38
2.03
3.60
3.45
163.1
178.3
167.6
171.6
171.5
156.7
171.8
87.9
88.9
164.7
173.8
159.2
168.7
123.9
123.8
179.0
69.8
176.4
175.9
178.2
151.2
168.3
180.0
155.8
143.3
151.4
154.0
145.4
141.1
164.2
161.1
179.3
158.0
176.2
176.2
147.1
140.6
72.8
72.8
173.0
177.0
143.6
48.2
125.8
125.8
125.8
125.8
162.9
155.6
176.0
111.4
168.9
180.0
127.1
139.1
126.8
136.8
151.7
43.1
56.3
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH 3 ) 2 (47)
-4.62
-2.93
-3.56
-4.17
-2.96
-1.68
0.45
-0.03
1.87
OHH...CH3 SSCH3 , cyclic (48)
HOH...Thiophene (49)
-3.78
-2.66
-1.20
-4.61
2.59
-1.95
HOH...SHC6 H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3 COOH...NH3 , bidentate (53)
-2.20
-0.96
-2.27
-11.94
-5.63
-1.39
-2.31
-5.56
-3.43
-0.43
-0.04
6.37
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH (55)
-10.69
-15.48
-11.75
-12.82
-1.06
2.66
Methylethylhydroxylamine...OH2 (56)
-7.41
-8.95
-1.54
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2 NH...O(CH3 ) 2 (59)
Methylammonium...OH2 (60)
Guanidinium...OHH (61)
-4.87
-3.09
-3.12
-19.30
-18.48
-3.52
-2.72
-3.51
-20.25
-20.18
1.35
0.37
-0.39
-0.95
-1.70
Imidazolium...OH2 (62)
OHH...(-)O2 CCH3 , bidentate (66)
-16.95
-21.85
-17.18
-17.23
-0.23
4.62
a
2.94
3.33
3.12
3.12
3.38
3.59
3.59
4.56
4.15
3.47
2.63
2.89
2.63
2.49
2.64
2.66
2.66
2.70
3.34
3.00
2.70
2.85
2.85
2.71
2.77
2.78
3.01
3.08
3.24
3.24
3.42
3.21
3.21
3.30
3.22
3.15
2.95
2.86
2.78
2.84
2.76
2.74
3.10
3.08
3.55
3.02
2.76
2.88
2.88
2.88
2.93
2.93
0.07
-0.25
0.13
0.13
0.04
-0.39
-0.39
-1.26
-0.93
-0.32
0.33
-0.03
0.15
0.36
0.12
0.08
0.44
0.37
0.21
0.02
0.06
0.03
0.03
0.18
0.16
0.15
2.20
2.29
3.13
3.13
2.84
3.50
3.33
4.27
3.19
2.83
1.90
2.53
1.94
1.83
2.17
2.11
2.18
2.06
2.82
2.32
1.79
2.08
2.08
1.81
2.06
2.08
2.41
2.34
2.77
2.78
3.19
3.13
2.38
2.45
2.48
2.36
2.08
1.89
1.96
1.97
1.96
2.99
3.20
2.23
2.72
2.01
1.88
1.97
1.97
1.94
2.11
2.11
173.2
175.3
97.7
97.7
147.0
108.4
121.0
132.4
175.5
175.5
168.3
119.0
161.0
148.9
124.2
138.5
130.2
153.9
143.5
155.9
173.8
147.7
147.7
174.5
142.9
141.8
117.7
111.0
111.2
110.7
95.4
86.2
143.2
146.9
111.7
139.1
151.5
157.9
141.9
148.0
130.4
65.7
75.0
146.4
145.4
178.4
140.5
148.1
148.1
159.0
140.6
140.6
For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17, 520-552 (1996).
TABLE SM-VII. ________________________________________________________________________________
CHARMM 22a vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Dimer (Structure Number)b
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
-6.47
-5.02
-6.83
-5.21
-0.36
-0.19
HOH...OHCH3 (3)
CH3 OH...OH2 (4)
CH3 OH...OHCH3 (5)
HOH...O(CH3 ) 2 (6)
C6 H5 OH...OH2 (7)
HOH...OHC6 H5 (8)
H3 CCOOH...HOOCCH3 , cyclic (12)
-6.10
-6.15
-6.09
-5.84
-8.10
-5.18
-17.10
-7.06
-6.64
-6.99
-6.50
-8.08
-5.34
-14.06
-0.96
-0.49
-0.90
-0.66
0.03
-0.16
3.04
H3 CCOOH...OHH (13)
-10.94
-10.16
0.77
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-5.97
-8.03
-14.78
-6.16
-8.37
-12.65
-0.19
-0.34
2.13
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-3.86
-7.67
-8.06
-6.28
0.45
-0.36
-2.42
H2 NH...HNH2 , cyclic C2h (32)
-3.51
-3.29
0.22
H2 NH...NH3 , linear Cs (33)
-3.38
-3.60
-0.22
HOH...NH3 (34)
-7.22
-6.67
0.54
2.73
2.58
2.