SMTables.doc 389KB Jun 05 2011 09:30:49 PM
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*
OPLS*
MM2*
MM3*
N-methylformamide, cis - trans
1.03
1.09
1.28
1.83
3.44#
1.57
0.41
0.46
1.50
N-methylactamide, cis - trans
1.90
1.97
2.18
3.09
2.46
2.33
1.98
1.74
2.31
N-formylformamide,
o=c-n-h cis,trans - cis,cis
0.41
0.44
0.40
0.95
2.68#
0.37
-0.98
-1.10#
1.72
glycine dipeptide analog, C5 - C7
0.91
1.08
1.14
-0.16
2.13
1.29
0.37
5.24##
0.65
alanine dipeptide analog, C5 - C7eq
1.08
1.11
1.12
0.76
2.58#
1.68
1.69
5.52##
0.00
alanine dipeptide analog, C7ax - C7eq
2.20
1.58
1.83
1.43
1.43
1.72
2.98
1.36
1.16
alanine dipeptide analog, '- C7eq
4.88
5.24
4.85
4.54
7.04#
6.22
4.32
---
3.60
alanine dipeptide analog, 2' - C7eq
2.76
---
2.47
---
---
---
1.84
---
---
alanine dipeptide analog, L - C7eq
4.10
4.28
3.87
---
---
---
---
---
1.16#
N-OH,N-methylacetamide,
o-n-c=o cis - trans
0.04
-0.19
0.01
1.95#
---
---
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]
0.24
0.53
0.14
-1.97#
2.55#
---
---
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]
1.50
---
1.56
-2.39##
---
---
9.32##
---
---
N-OH,N-Et acetamide,
[o-n-c=o cis, c-c-n-c(=o) sk] -
0.08
---
0.27
---
0.04
---
---
---
---
Conformational comparison
Amides:
-5.40## -5.03## -9.38##
4.81## 10.08##
[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]
0.04
0.24
0.08
-2.21#
3.82##
5.17##
9.46##
---
---
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
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]
0.96
1.24
1.07
-2.41##
3.42#
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]
0.72
1.24
1.09
0.26
0.26
---
glycine dipeptide, C5 - C7
1.66
1.40
1.62
1.08
2.55
alanine dipeptide, C5 - C7eq
1.64
1.42
1.68
1.79
alanine dipeptide, C7ax - C7eq
2.20
1.84
2.26
alanine dipeptide, ' - C7eq
5.35
5.66
alanine dipeptide, 2 - C7eq
3.20
alanine dipeptide, L - C7eq
Conformational comparison
AMBER*
OPLS*
5.17## 11.29##
MM2*
MM3*
---
---
2.19
---
---
-1.20#
-0.70#
5.65##
1.25
2.93
-0.69#
0.44
6.05##
0.56
1.17
1.84
2.19
2.95
1.53
1.34
5.47
5.34
7.30#
---
5.48
---
4.26
---
3.06
---
---
---
---
---
---
4.25
4.74
4.75
---
---
---
---
---
---
formic acid, trans - cis
4.79
4.89
4.89
4.48
5.97
6.55#
7.64#
11.38##
4.89
acetic acid, trans - cis
5.86
5.87
5.87
6.05
4.76
7.23
6.67
13.66##
5.70
propanoic acid, c-c-c=o sk - cis
0.85
0.84
0.84
0.90
0.80
-0.22
-0.10
0.52
0.71
gyloxylic acid,
[o=c-c=o trans, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
0.35
1.91#
1.91#
2.94#
0.89
1.07
glycolic acid, o=c-c-o sk - cis
1.64
0.80
0.80
2.57
-2.76## -0.71#
-3.50##
propenoic acid, c=c-c=o trans - cis
0.21
0.25
0.25
0.70
-0.39
-0.14
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,cis] -
2.22
0.97
0.97
6.22##
7.46##
Carboxylic Acids:
-0.03
0.01#
5.08## -5.68## -0.49
0.94
2.88
-0.05
-1.17
9.84## -8.85## -1.74##
[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]
1.65
1.90
1.90
3.94##
4.05##
1.34
6.30## -2.61## -0.34#
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
1.67
2.42
2.42
2.97
2.48
1.52
4.42#
methyl formate, o=c-o-c trans - cis
5.65
5.28
5.28
5.09
5.54
1.34##
0.87##
5.61
2.18##
methyl acetate, o=c-o-c trans - cis
vinyl formate, c=c-o-c cis - trans
8.21
8.27
8.27
8.67
9.09
7.42
7.47
6.68#
7.85
ethyl formate, c-o-c-c g - a
2.79
2.83
2.83
---
4.79#
---
---
2.84
---
0.34
0.44
0.44
0.67
---
0.99
0.69
0.27
0.23
isopropyl formate, c-c-o-c g,g - g,a
2.43
2.43
2.43
2.16
5.58##
2.65
2.84
0.74#
1.60
phenyl acetate, o=c-o-c cis - trans
4.30
4.50
4.50
2.58#
1.32#
2.06#
4.93
8.80##
1.28##
methyl glycolate, o=c-c-o sk - cis
1.48
2.43
2.43
2.40
-3.25##
0.35
-0.03#
2.22
2.84
1,3-butadiene, g - s-trans
2.39
2.46
2.46
3.39
2.39
2.45
2.80
2.74
1.72
2-methyl-1,3-butadiene, g - s-trans
2.20
2.12
2.12
2.79
1.95
3.29
1.85
2.49
1.63
2-methyl-but-1-ene-3-one,
c=c-c=o cis - trans
2.08
1.90
1.90
-0.42#
2.46
-0.57#
1.37
1.66
1.95
2-methylpropenamide, c=c-c=o cis - sk
1.05
1.04
1.00
-0.42
6.08## -3.13##
0.16
2.90#
1.04
propenamide, c=c-c=o sk - cis
0.61
0.57
0.60
0.31
but-1-ene-3-one, c=c-c=o cis - trans
0.43
0.28
0.28
0.69
0.58
acrolein, c=c-c=o cis - trans
2.03
2.05
2.05
1.59
2-methylpropenal, c=c-c=o cis - trans
3.14
3.15
3.15
-0.07##
Conformational comparison
pyruvic acid,
[o=c-c=o cis, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
MM2*
MM3*
-4.13## -0.16#
Esters:
Congujated systems:
-3.02## -1.77#
-2.26#
-0.84
-0.79
0.67
1.43
0.50
0.71
2.47
2.03
1.69
1.64
1.98
5.50#
1.40#
0.64#
3.25
3.46
2-methylpropenoic acid,
c=c-c=o cis - trans
0.60
0.62
0.62
-0.45
0.71
-0.52
0.38
-1.18#
1.30
1,3-pentadiene,
[c=c-c=c g, c-c=c-c trans] [c=c-c=c s-trans, c-c=c-c trans]
2.43
2.46
2.46
3.24
2.56
2.70
3.19
2.83
1.83
"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
propionaldehyde, c-c-c=o sk - cis
0.83
0.53
0.53
1.09
0.32
1.65
-0.46
0.90
1.10
2-butanone c-c-c=o sk - cis
0.98
0.83
0.83
1.35
0.19
1.73
-0.04
1.57
1.61
methyl ispropyl ketone,
o=c-c(ch3)2-h cis - trans
0.69
0.89
0.89
1.24
0.87
1.65
0.40
1.36
1.53
butyraldehyde, c-c-c-c g - a
0.14
0.11
0.11
0.87
0.89
1.27
1.08
0.84
0.91
but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk+, c-c-c=o sk+]
0.20
-0.05
-0.05
---
1.16
-0.96
-0.11
0.95
2.11#
but-3-enal,
[c=c-c-c sk-, c-c-c=o sk+] [c=c-c-c sk+, c-c-c=o sk+]
0.29
0.98
0.98
0.65
0.71
0.51
0.62
0.07
0.51
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]
0.43
0.72
0.72
0.06
1.34
0.08
1.31
1.25
2.68#
isobutyraldehyde, h-c(=0)-c-h a - g
0.37
0.56
0.56
0.97
0.04
1.58
-0.49
0.99
1.16
2-formylpropanal, o-c-c-c(=o) a - g
0.18
0.14
0.14
0.01
-1.94#
0.25
-0.33
4-oxobutanal (o=c-c-c, c-c-c=o cis, cis),
c-c-c-c s-trans - g
0.70
0.77
0.77
-1.34#
-0.98#
2.14
0.03
-0.24
-1.37#
2,3-butanedione, c-c-c-c g - s-trans
5.40
---
---
3.51#
4.66
---
---
Conformational comparison
1,3-pentadiene,
[s-trans, c-c=c-c cis] [s-trans, c-c=c-c trans]
Aldehydes and ketones:
-3.85## -2.60#
7.12#
2.88#
Halides:
1,2-difluoroethane, a - g
0.58
0.63
0.63
-1.57#
1.05
-1.16#
-0.93#
0.01
0.04
1,2-dicloroethane, g - a
1.29
1.24
1.24
1.22
1.47
1.13
0.87
1.13
1.95
1-fluoropropane, a - g
0.03
0.06
0.06
-0.93
-0.12
0.03
-0.41
-0.08
-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
formamidine (N puckered),
h-n=c-n cis - trans
2.03
2.03
2.27
1.62
2.08
1.78
4.23#
-0.96#
-0.68#
N-methylformamidine (N puckered),
n-c=n-c cis - trans
2.00
2.00
2.12
2.67
-3.12##
3.82#
---
-0.09#
1.03
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]
1.73
1.94
1.94
6.58##
2.63
1.96
1.89
2.60
1.99
2-methoxytetrahydropyran,
[eq, me-o-c-c a] - [ax, me-o-c-c a]
1.30
1.81
1.81
1.88
2.37
0.97
1.70
2.27
1.63
2,4-dioxapentane,
[c-o-c-o g, o-c-o-c a] [c-o-c-o g+, o-c-o-c g+]
2.44
2.11
2.11
2.54
3.37
2.95
1.93
2.99
2.26
2,5-dimethyl-1,3-dioxane, 5-ax - 5-eq
0.63
0.50
0.50
0.04
-0.65
-0.67
0.41
0.69
0.75
methoxymethanol,
[c-o-c-o g+, o-c-o-h g-] [c-o-c-o g+, o-c-o-h g+]
2.25
2.97
2.97
1.96
-3.98##
2.34
2.86
2.84
2.94
N-proplyamine cation, c-c-c-n g - a
0.07
0.03
0.03
0.29
-0.32
-0.65
0.34
0.99
1.12
ethylguanidine cation, c-c-n=c g - a
0.62
0.38
0.38
---
-1.37#
-0.18
0.33
0.11
---
Conformational comparison
1-chloropropane, g - a
Imines, guanidines, and amidines
Ketals, acetals, and hemiacetals:
Cations:
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
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
isopropylamine,
[C1, h-c-n-lp g] [Cs, h-c-n-lp a]
0.50
0.45
0.45
0.16
-0.07
0.23
0.00
0.15
0.22
cyclohexylamine, ax - eq
0.69
0.67
0.67
0.83
1.78
-0.74
0.62
1.38
1.23
piperidine, n-h ax - eq
0.78
0.90
0.90
0.05
0.13
0.14
-0.04
0.31
0.31
N-methylpiperidine, ax - eq
3.58
3.28
3.28
3.25
2.70
1.26#
2.32
2.53
2.31
ethylamine, c-c-n-lp a - g
0.08
0.44
0.44
0.20
0.22
0.26
0.00
0.14
0.12
3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
0.50
0.51
0.51
2.44#
0.00
-0.84
-1.07#
0.71
1.82
3-aminopropene,
[c=c-c-n sk, c-c-n-lp a] [c=c-c-n sk, c-c-n-lp g]
0.15
0.65
0.65
-0.17
-0.21
-0.18
0.68
-0.30
-0.08
2-methyl,3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
0.67
0.61
0.61
1.19
0.47
0.32
-0.93#
1.03
1.75
ethylenediamine,
[n-c-c-n a, c-c-n-lp g+, g+] [n-c-c-n g+, c-c-n-lp g+, g+]
1.39
1.45
1.45
0.84
1.48
1.20
0.59
methylethylamine N-oxide, c-n-c-c g - a
1.38
1.41
1.41
-0.73#
3.62#
1.23
---
---
---
methylethylhydroxylamine, c-n-c-c g - a
1.69
2.25
2.25
1.63
1.76
1.17
1.61
1.20
---
ethylamine N-oxide, o-n-c-c a - g
0.68
0.73
0.73
-1.61#
1.61
0.68
---
---
---
ethylhydroxylamine, o-n-c-c a - g
0.20
0.05
0.05
-0.57
2.98#
0.55
-0.28
-0.05
---
Conformational comparison
12.94## 21.84##
Alcohols:
ethanol, a - g
0.06
-0.18
-0.18
-0.37
-0.23
-0.36
0.00
-0.60
-0.41
n-propanol,
[c-c-c-o g-, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
0.23
0.58
0.58
-0.42
0.02
-0.76
0.28
0.36
0.60
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
n-propanol,
[c-c-c-o g+, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
0.05
0.24
0.24
0.01
-0.43
-0.62
0.28
0.36
0.35
n-propanol,
[c-c-c-o a, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
0.20
-0.17
-0.17
-0.49
-0.16
-0.30
0.00
-0.60
-0.42
n-propanol,
[c-c-c-o g, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
0.10
0.12
0.12
-0.23
-0.29
-0.81
0.28
-0.30
-0.06
isopropanol, h-c-o-h a - g
0.20
0.17
0.17
0.40
0.02
0.25
0.00
0.61
0.68
cyclopentanol, eq Cs - ax C1
1.11
0.82
0.82
-0.27
---
-0.36
-0.07
0.40
0.89
cyclopentanol, ax Cs- ax C1
1.05
0.59
0.59
-0.33
-0.94#
---
0.00
0.82
1.35
cyclopentanol, eq C1 - ax C1
1.14
0.47
0.47
-0.53#
-0.62#
0.70
-0.07
-0.23
-0.15
cyclohexanol, eq Cs - eq C1
0.18
0.20
0.20
0.38
0.06
0.15
0.00
0.62
0.77
cyclohexanol, ax Cs - eq C1
1.14
1.01
1.01
-0.49#
0.58
-0.87#
0.50
1.46
2.43
cylohexanol, ax C1 - eq C1
0.33
0.32
0.32
0.24
0.40
-0.57
0.50
0.58
0.74
vinyl alcohol, c=c-o-h trans - sk
1.43
1.43
1.43
1.58
0.66
-0.81#
-0.69#
1.75
-0.09#
benzyl alcohol, h-o-c-c a - g
1.13
1.59
1.59
1.38
2.97#
0.81
1.23
1.22
1.33
propen-3-ol,
[c=c-c-o sk, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
1.24
1.10
1.10
0.82
2.43
1.07
0.19
1.20
1.12
propen-3-ol,
[c=c-c-o cis, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
1.11
1.13
1.13
3.39#
0.49
-0.08
-1.06#
0.83
2.76#
Conformational comparison
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]
0.38
0.47
0.47
0.94
0.39
-0.71
-1.57#
-0.10
1.53
sec-butanol, ga/ga - ga/aga
0.10
0.33
0.33
-0.62
0.23
-0.30
0.00
0.07
0.24
sec-butanol, ga/gg - ga/ag
0.18
0.11
0.11
0.23
-0.32
0.05
0.00
0.64
0.69
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
sec-butanol, ag/ag - ga/ag
0.48
0.47
0.47
0.57
1.02
0.93
0.71
0.53
0.49
sec-butanol, ag/ga - ga/ag
0.29
0.46
0.46
0.74
1.06
0.85
0.71
0.53
0.50
sec-butanol, ag/gg - ga/ag
0.56
0.59
0.59
1.15
0.87
1.07
0.71
1.14
1.14
sec-butanol, gg/ag - ga/ag
0.75
0.72
0.72
0.87
0.79
0.40
1.00
0.82
0.98
sec-butanol, gg/ga - ga/ag
0.57
0.66
0.66
0.68
0.43
0.20
1.00
0.90
0.97
sec-butaone, gg/gg - ga/ag
1.13
1.14
1.14
0.56
1.01
0.33
1.00
1.54
2.06
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]
2.71
2.91
2.91
0.70#
2.45
5.69#
17.30##
2.30
0.80#
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]
0.49
1.15
1.15
1.45
0.79
0.29
---
1.47
---
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]
1.41
1.58
1.58
1.92
1.17
0.37
---
1.50
---
methyl ethyl ether, g - a
1.41
1.50
1.50
1.46
1.53
1.79
1.85
1.74
1.48
methyl vinyl ether, c=c-o-c skew - cis
2.27
2.22
2.22
-3.10##
2.10
1.07
0.60#
diethyl ether,
[c-c-o-c a, c-o-c-c g] [c-c-o-c a, c-o-c-c a]
1.48
1.52
1.52
1.37
1.55
1.83
1.84
1.77
1.49
methoxycyclohexane, eq Cs - ax C1
2.10
1.95
1.95
2.19
1.56
2.76
2.08
1.53
1.80
methoxycyclohexane, eq C1 - ax C1
0.01
-0.41
-0.41
0.11
-0.70
0.34
-0.37
-0.56
-0.76
Conformational comparison
Ethers:
-2.90## -3.94##
methyl isopropyl ether, h-c-o-ch3 a - g
1.91
1.88
1.88
2.10
1.91
2.25
2.20
1.73
2.12
0.65
0.78
0.78
0.89
0.78
0.39
0.95
0.86
0.81
Alkanes:
butane, g - a
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
cyclohexane, twist-boat - chair
6.14
5.93
5.93
7.08
6.72
5.79
6.77
5.36
5.76
methylcyclohexane, ax - eq
1.69
1.37
1.37
1.84
1.80
0.90
1.78
1.78
1.77
2,3-dimethylbutane, h-c2-c3-h g - a
0.04
-0.23
-0.23
0.13
0.40
-0.22
-0.48
0.15
0.38
cyclooctane, D4d crown - Cs boat-chair
2.00
1.44
1.44
1.21
0.45#
0.83
-1.67##
0.96
1.12
cyclooctane,
C2 twist-boat-chair - Cs boat-chair
1.71
1.99
1.99
2.30
1.88
1.77
1.20
1.66
1.85
cyclooctane, S4 - Cs boat-chair
2.97
3.27
3.27
0.16#
4.48#
3.63
6.51##
3.12
2.62
methylcyclobutane, ax - eq
0.77
0.78
0.78
1.21
0.06
0.17
0.63
0.58
0.92
cyclononane, C2 [144] - D3 [333]
1.97
1.41
1.41
1.02
0.37#
0.53
-1.02#
0.77
1.15
cyclononane, C2 [225] - D3 [333]
0.99
1.21
1.21
-1.63#
1.12
1.07
0.80
0.75
0.84
cyclononane, C1 [234] - D3 [333]
3.65
3.81
3.81
2.03#
3.45
3.66
4.31
3.16
3.04
1-butene, c=c-c-c cis - sk
0.26
0.26
0.26
0.72
0.46
0.66
1.00
0.49
0.68
1-pentene (c=c-c-c skew),
c-c-c-c g - a
0.61
0.51
0.51
0.90
-0.10
0.11
0.60
0.78
0.42
2-methyl-1-butene, c=c-c-c skew - cis
0.02
-0.03
-0.03
-0.07
-0.93
-0.97
-0.98
-0.06
-0.38
1,4-pentadiene,
c=c-c-c sk+,sk- - sk-,sk-
0.33
0.43
0.43
0.33
0.19
0.44
0.25
0.07
0.27
2-butene, cis - trans
1.27
1.35
1.35
1.43
1.61
1.55
2.49
1.43
1.02
2-pentene,
[c-c=c-c cis, c-c-c=c sk] [c-c=c-c trans, c-c-c=c sk]
1.31
1.33
1.33
1.35
1.61
1.43
2.39
1.29
0.99
Conformational comparison
Alkenes:
Thiols, sulfides, and disulfides:
ethanethiol, c-c-s-h a - g
0.74
0.68
0.68
0.33
-0.78#
-0.20
0.00
0.28
-0.04
ethyl methyl disulfide, c-c-s-s a - g
0.76
0.76
0.76
-0.31
0.11
-1.29#
0.04
-0.19
0.05
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
1-propanethiol,
[s-c-c-c g-, h-s-c-c g+] [s-c-c-c a, h-s-c-c g]
0.30
0.37
0.37
1.59
-0.84
1.51
0.48
0.84
1.04
1-propanethiol,
[s-c-c-c g, h-s-c-c a] [s-c-c-c a, h-s-c-c g]
1.23
0.95
0.95
2.26
-1.65#
1.53
0.48
0.92
0.65
1,2-ethanedithiol,
[all anti] [h-s-c-c a,g+, s-c-c-s g-]
0.86
1.17
1.17
0.15
-0.95#
6.92##
5.17#
-0.92#
-1.71#
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-]
1.77
2.24
2.24
1.71
0.26#
1.62
5.51##
0.68
0.34
methyl propyl sulfide,
[c-s-c-c g-, s-c-c-c g-] [c-s-c-c g, s-c-c-c a]
0.09
0.05
0.05
1.56
-0.08
1.21
0.12
0.58
0.61
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c g] [c-s-c-c g, s-c-c-c a]
0.66
0.60
0.60
-0.03
0.18
0.94
-0.24
0.24
0.51
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c a] [c-s-c-c g, s-c-c-c a]
0.25
0.33
0.33
-1.66#
0.23
-0.24
-0.43
-0.39
-0.18
Conformational comparison
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.61
-0.14
2.73
2.75
0.02
2.03
1.78
172.3
170.4
HOH...HOH, cyclic Cs (2)
-5.02
-4.91
0.11
2.58
2.78
0.19
2.31
2.19
111.8
117.0
2.58
2.78
0.19
2.31
2.19
111.8
117.0
HOH...OHCH3 (3)
-6.10
-6.33
-0.23
2.72
2.73
0.02
2.01
1.76
169.0
168.7
CH3OH...OH2 (4)
-6.15
-6.15
0.00
2.72
2.75
0.03
2.01
1.76
174.9
179.9
CH3OH...OHCH3 (5)
-6.09
-6.04
0.05
2.71
2.73
0.02
2.00
1.74
174.6
177.0
HOH...O(CH3)2 (6)
-5.84
-5.98
-0.14
2.71
2.77
0.06
2.02
1.81
163.9
166.7
C6H5OH...OH2 (7)
-8.10
-8.45
-0.35
2.67
2.69
0.02
1.95
1.72
174.0
167.5
HOH...OHC6H5 (8)
-5.18
-5.08
0.10
2.79
2.83
0.04
2.12
1.89
160.8
159.9
t-Vinyl alcohol...OH2 (9)
-8.18
-8.48
-0.30
2.65
2.68
0.02
1.93
1.69
175.0
176.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.46
-0.30
2.79
2.81
0.02
2.11
1.87
163.2
160.4
HOH...Furan (11)
-4.00
-3.78
0.22
2.78
2.88
0.10
2.22
1.97
141.6
155.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-17.09
0.01
2.57
2.57
2.62
2.62
0.05
0.05
1.83
1.83
1.63
1.63
175.9
175.9
169.2
169.2
H3CCOOH...OHH (13)
-10.94
-11.70
-0.76
2.58
2.61
2.64
2.77
0.07
0.16
1.90
2.15
1.67
2.11
156.3
127.9
163.4
122.8
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
2.54
2.61
2.61
2.60
0.07
-0.02
1.80
2.22
1.61
1.92
171.5
122.2
175.4
123.9
-4.90
-6.10
-1.20
2.97
2.96
2.94
2.79
-0.04
-0.17
2.44
2.35
2.02
2.69
141.1
151.7
155.7
85.4
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
2.90
3.21
2.86
3.20
-0.04
-0.01
2.27
2.95
2.02
2.43
155.0
117.5
142.6
135.5
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.80
0.40
2.73
2.87
0.14
2.08
1.94
155.6
159.0
HOH...Methyl formate (=O) (18)
-6.39
-6.84
-0.45
2.76
2.73
-0.03
2.06
1.75
167.0
177.6
HOH...Methyl formate (-O-) (19)
-3.82
-2.62
1.20
2.78
2.95
0.17
2.24
2.12
138.7
142.0
HOH...Formaldehyde (20)
-5.81
-6.74
-0.93
2.72
2.71
0.00
2.11
1.74
147.6
170.5
HOH...Acetone (21)
-6.87
-7.06
-0.19
2.74
2.71
-0.03
2.06
1.73
163.1
173.1
t-NMA...OH2 (22)
-5.97
-6.86
-0.89
2.87
2.84
-0.03
2.12
1.82
178.3
176.9
HOH...t-NMA (23)
-8.03
-8.19
-0.16
2.70
2.71
0.00
2.00
1.73
167.6
174.2
-14.78
-12.26
2.52
2.76
2.76
2.81
2.81
0.06
0.06
2.00
2.00
1.79
1.79
171.6
171.5
173.4
173.4
Formamide dimer, parallel (25)
-8.12
-7.69
0.43
2.80
2.76
-0.03
2.09
1.74
156.7
174.4
t-NMA dimer, antiparallel (26)
-7.70
-9.08
-1.38
2.83
2.76
-0.07
2.08
1.76
171.8
165.3
t-NMA antiparallel stacked (27)
-3.86
-5.62
-1.76
3.65
3.67
3.61
3.61
-0.05
-0.06
3.88
3.88
3.49
3.49
87.9
88.9
88.5
88.4
HOH...N-Methylformamide (28)
-7.90
-8.07
-0.17
2.71
2.71
0.00
2.01
1.73
164.7
174.8
N-Methylformamide...OH2 (29)
-6.05
-6.94
-0.89
2.84
2.82
-0.01
2.09
1.80
173.8
175.4
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-7.99
0.22
2.62
2.70
0.08
1.94
1.72
159.2
175.8
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-3.95
0.15
2.82
2.85
0.03
2.12
1.87
168.7
175.8
H2NH...HNH2, cyclic C2h (32)
-3.51
-3.02
0.49
3.01
3.01
3.11
3.11
0.10
0.10
2.60
2.61
2.40
2.40
123.9
123.8
125.4
125.4
H2NH...NH3, linear Cs (33)
-3.38
-3.67
-0.29
3.15
3.15
3.03
3.03
-0.12
-0.12
2.42
3.64
2.00
3.36
179.0
69.8
178.1
62.7
HOH...NH3 (34)
-7.22
-6.83
0.39
2.80
2.80
0.00
2.09
1.82
176.4
173.9
HOH...NH2CH3 (35)
-7.07
-6.70
0.37
2.80
2.82
0.02
2.09
1.84
175.9
173.1
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.91
-0.91
2.79
2.82
0.04
2.03
1.81
178.2
175.6
HOH...Imidazole (37)
-7.77
-7.93
-0.16
2.73
2.75
0.01
2.10
1.81
151.2
158.6
Indole...OH2 (38)
-6.33
-6.51
-0.18
2.81
2.86
0.05
2.07
1.84
168.3
179.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.86
0.04
2.07
1.84
180.0
180.0
HOH...Pyridine (40)
-6.63
-7.10
-0.47
2.77
2.79
0.02
2.12
1.85
155.8
158.9
Formamidine...H2O, cyclic (41)
-11.03
-10.65
0.38
2.81
2.70
2.97
2.76
0.15
0.06
2.20
2.06
2.09
1.80
143.3
151.4
142.8
162.0
HOH...Formaldehydeimine (42)
-6.74
-7.95
-1.21
2.76
2.74
-0.02
2.11
1.77
154.0
167.6
Guanidine...OHH (43)
-7.96
-7.47
0.49
2.88
2.77
2.90
2.94
0.02
0.18
2.25
2.21
1.98
2.11
145.4
141.1
148.1
141.1
Vinylamine...OH2 (44)
-3.80
-4.61
-0.81
3.04
2.87
-0.17
2.19
1.85
164.2
173.3
Aniline...OH2 (45)
-4.62
-4.86
-0.24
2.94
2.87
-0.06
2.20
1.85
173.2
172.8
HSH...OH2 (46)
-2.93
-2.91
0.02
3.33
3.38
0.05
2.29
2.03
175.3
172.8
HOH...S(CH3)2 (47)
-3.56
-3.48
0.08
3.12
3.12
3.35
3.35
0.23
0.23
3.13
3.13
2.38
3.62
97.7
97.7
170.8
66.4
OHH...CH3SSCH3, cyclic (48)
-3.78
-3.22
0.56
3.38
3.55
0.17
2.84
2.58
147.0
174.6
HOH...Thiophene (49)
-2.66
-2.71
-0.05
3.59
3.59
3.69
3.69
0.10
0.10
3.50
3.33
3.03
3.34
108.4
121.0
126.8
103.6
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.37
-0.19
4.27
3.55
132.4
144.2
HSH...SH2 (51)
-0.96
-1.25
-0.29
4.15
4.02
-0.13
3.19
2.70
175.5
167.3
HOH...SH2 (52)
-2.27
-2.00
0.27
3.47
3.49
0.02
2.83
2.55
175.5
163.2
CH3COOH...NH3, bidentate (53)
-11.94
-11.58
0.36
2.63
2.89
2.66
3.02
0.03
0.12
1.90
2.53
1.66
2.43
168.3
119.0
174.3
115.2
HOH...PyridineN-oxide (54)
-10.69
-10.61
0.08
2.63
2.64
0.01
1.94
1.65
161.0
178.6
MethylethylamineN-oxide...OHH( 55)
-15.48
-14.87
0.61
2.49
2.59
0.10
1.83
1.66
148.9
154.6
2.64
2.74
0.11
2.17
2.10
124.2
117.6
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
2.66
2.66
2.79
2.88
0.13
0.22
2.11
2.18
1.94
2.10
138.5
130.2
143.2
135.1
HOH...FCH3 (59)
-4.87
-4.48
0.39
2.70
2.66
-0.04
2.06
1.69
153.9
172.7
HOH...Chloropropane (58)
-3.09
-2.84
0.25
3.34
3.35
0.01
2.82
2.45
143.5
153.9
H2NH...O(CH3)2 (59)
-3.12
-3.43
-0.31
3.00
3.00
0.00
2.32
1.97
155.9
173.9
Methylammonium...OH2 (60)
-19.30
-21.17
-1.87
2.70
2.62
-0.08
1.79
1.57
173.8
176.7
Guanidinium...OHH (61)
-18.48
-19.02
-0.54
2.85
2.85
2.78
2.78
-0.07
-0.07
2.08
2.08
1.87
1.87
147.7
147.7
146.8
146.8
Imidazolium...OH2 (62)
-16.95
-17.60
-0.65
2.71
2.62
-0.08
1.81
1.59
174.5
173.4
Formamidinium...OH2 (63)
-16.98
-18.75
-1.77
2.71
2.61
-0.10
1.91
1.57
148.7
177.2
Formamidinium...OH2, cyclic C2v (64)
-19.59
-19.71
-0.12
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
Formaldehydeiminium...OH2 (65)
-19.98
-21.65
-1.67
2.66
2.65
-0.01
1.78
1.61
163.4
176.6
OHH...(-)O2CCH3, bidentate (66)
-21.85
-22.62
-0.77
2.77
2.78
2.74
2.74
-0.03
-0.03
2.06
2.08
1.87
1.87
142.9
141.8
145.7
145.7
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.61
-0.14
2.73
2.75
0.02
2.03
1.78
172.3
170.4
HOH...HOH, cyclic Cs (2)
-5.02
-4.91
0.11
2.58
2.78
0.19
2.31
2.19
111.8
117.0
2.58
2.78
0.19
2.31
2.19
111.8
117.0
HOH...OHCH3 (3)
-6.10
-6.33
-0.23
2.72
2.73
0.02
2.01
1.76
169.0
168.7
CH3OH...OH2 (4)
-6.15
-6.15
0.00
2.72
2.75
0.03
2.01
1.76
174.9
179.9
CH3OH...OHCH3 (5)
-6.09
-6.04
0.05
2.71
2.73
0.02
2.00
1.74
174.6
177.0
HOH...O(CH3)2 (6)
-5.84
-5.98
-0.14
2.71
2.77
0.06
2.02
1.81
163.9
166.7
C6H5OH...OH2 (7)
-8.10
-8.45
-0.35
2.67
2.69
0.02
1.95
1.72
174.0
167.5
HOH...OHC6H5 (8)
-5.18
-5.08
0.10
2.79
2.83
0.04
2.12
1.89
160.8
159.9
t-Vinyl alcohol...OH2 (9)
-8.18
-8.48
-0.30
2.65
2.68
0.02
1.93
1.69
175.0
176.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.46
-0.30
2.79
2.81
0.02
2.11
1.87
163.2
160.4
HOH...Furan (11)
-4.00
-3.78
0.22
2.78
2.88
0.10
2.22
1.97
141.6
155.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-17.09
0.01
2.57
2.57
2.62
2.62
0.05
0.05
1.83
1.83
1.63
1.63
175.9
175.9
169.2
169.2
H3CCOOH...OHH (13)
-10.94
-11.70
-0.76
2.58
2.61
2.64
2.77
0.07
0.16
1.90
2.15
1.67
2.11
156.3
127.9
163.4
122.8
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
2.54
2.61
2.61
2.60
0.07
-0.02
1.80
2.22
1.61
1.92
171.5
122.2
175.4
123.9
-4.90
-6.10
-1.20
2.97
2.96
2.94
2.79
-0.04
-0.17
2.44
2.35
2.02
2.69
141.1
151.7
155.7
85.4
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
2.90
3.21
2.86
3.20
-0.04
-0.01
2.27
2.95
2.02
2.43
155.0
117.5
142.6
135.5
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.80
0.40
2.73
2.87
0.14
2.08
1.94
155.6
159.0
HOH...Methyl formate (=O) (18)
-6.39
-6.84
-0.45
2.76
2.73
-0.03
2.06
1.75
167.0
177.6
HOH...Methyl formate (-O-) (19)
-3.82
-2.62
1.20
2.78
2.95
0.17
2.24
2.12
138.7
142.0
HOH...Formaldehyde (20)
-5.81
-6.74
-0.93
2.72
2.71
0.00
2.11
1.74
147.6
170.5
HOH...Acetone (21)
-6.87
-7.06
-0.19
2.74
2.71
-0.03
2.06
1.73
163.1
173.1
t-NMA...OH2 (22)
-5.97
-6.87
-0.90
2.87
2.84
-0.03
2.12
1.81
178.3
179.9
HOH...t-NMA (23)
-8.03
-8.25
-0.22
2.70
2.70
0.00
2.00
1.72
167.6
174.3
-14.78
-12.26
2.52
2.76
2.76
2.81
2.81
0.06
0.06
2.00
2.00
1.79
1.79
171.6
171.5
173.4
173.4
Formamide dimer, parallel (25)
-8.12
-7.69
0.43
2.80
2.76
-0.03
2.09
1.74
156.7
174.1
t-NMA dimer, antiparallel (26)
-7.70
-9.06
-1.36
2.83
2.76
-0.07
2.08
1.75
171.8
166.8
t-NMA antiparallel stacked (27)
-3.86
-5.33
-1.47
3.65
3.67
3.64
3.64
-0.01
-0.02
3.88
3.88
3.54
3.54
87.9
88.9
88.0
88.0
HOH...N-Methylformamide (28)
-7.90
-8.14
-0.24
2.71
2.71
0.00
2.01
1.73
164.7
174.9
N-Methylformamide...OH2 (29)
-6.05
-6.90
-0.85
2.84
2.83
-0.01
2.09
1.80
173.8
175.5
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.30
-0.09
2.62
2.70
0.08
1.94
1.72
159.2
177.0
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-4.26
-0.16
2.82
2.84
0.03
2.12
1.87
168.7
178.2
H2NH...HNH2, cyclic C2h (32)
-3.51
-3.02
0.49
3.01
3.01
3.11
3.11
0.10
0.10
2.60
2.61
2.40
2.40
123.9
123.8
125.4
125.4
H2NH...NH3, linear Cs (33)
-3.38
-3.67
-0.29
3.15
3.15
3.03
3.03
-0.12
-0.12
2.42
3.64
2.00
3.36
179.0
69.8
178.1
62.7
HOH...NH3 (34)
-7.22
-6.83
0.39
2.80
2.80
0.00
2.09
1.82
176.4
173.9
HOH...NH2CH3 (35)
-7.07
-6.70
0.37
2.80
2.82
0.02
2.09
1.84
175.9
173.1
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.91
-0.91
2.79
2.82
0.04
2.03
1.81
178.2
175.6
HOH...Imidazole (37)
-7.77
-7.93
-0.16
2.73
2.75
0.01
2.10
1.81
151.2
158.6
Indole...OH2 (38)
-6.33
-6.51
-0.18
2.81
2.86
0.05
2.07
1.84
168.3
179.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.86
0.04
2.07
1.84
180.0
180.0
HOH...Pyridine (40)
-6.63
-7.10
-0.47
2.77
2.79
0.02
2.12
1.85
155.8
158.9
Formamidine...H2O, cyclic (41)
-11.03
-10.68
0.35
2.81
2.70
2.97
2.77
0.16
0.07
2.20
2.06
2.13
1.80
143.3
151.4
137.8
167.5
HOH...Formaldehydeimine (42)
-6.74
-7.95
-1.21
2.76
2.74
-0.02
2.11
1.77
154.0
167.6
Guanidine...OHH (43)
-7.96
-7.02
0.94
2.88
2.77
2.88
3.22
0.00
0.46
2.25
2.21
1.88
3.84
145.4
141.1
165.7
45.0
Vinylamine...OH2 (44)
-3.80
-4.23
-0.43
3.04
2.88
-0.16
2.19
1.85
164.2
176.9
Aniline...OH2 (45)
-4.62
-4.54
0.08
2.94
2.88
-0.06
2.20
1.86
173.2
174.9
HSH...OH2 (46)
-2.93
-2.91
0.02
3.33
3.38
0.05
2.29
2.03
175.3
172.8
HOH...S(CH3)2 (47)
-3.56
-3.48
0.08
3.12
3.12
3.35
3.35
0.23
0.23
3.13
3.13
2.38
3.62
97.7
97.7
170.8
66.4
OHH...CH3SSCH3, cyclic (48)
-3.78
-3.22
0.56
3.38
3.55
0.17
2.84
2.58
147.0
174.6
HOH...Thiophene (49)
-2.66
-2.71
-0.05
3.59
3.59
3.69
3.69
0.10
0.10
3.50
3.33
3.03
3.34
108.4
121.0
126.8
103.6
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.37
-0.19
4.27
3.55
132.4
144.2
HSH...SH2 (51)
-0.96
-1.25
-0.29
4.15
4.02
-0.13
3.19
2.70
175.5
167.3
HOH...SH2 (52)
-2.27
-2.00
0.27
3.47
3.49
0.02
2.83
2.55
175.5
163.2
CH3COOH...NH3, bidentate (53)
-11.94
-11.58
0.36
2.63
2.89
2.66
3.02
0.03
0.12
1.90
2.53
1.66
2.43
168.3
119.0
174.3
115.2
HOH...PyridineN-oxide (54)
-10.69
-10.61
0.08
2.63
2.64
0.01
1.94
1.65
161.0
178.6
MethylethylamineN-oxide...OHH (55)
-15.48
-14.87
0.61
2.49
2.59
0.10
1.83
1.66
148.9
154.6
2.64
2.74
0.11
2.17
2.10
124.2
117.6
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
2.66
2.66
2.79
2.88
0.13
0.22
2.11
2.18
1.94
2.10
138.5
130.2
143.2
135.1
HOH...FCH3 (59)
-4.87
-4.48
0.39
2.70
2.66
-0.04
2.06
1.69
153.9
172.7
HOH...Chloropropane (58)
-3.09
-2.84
0.25
3.34
3.35
0.01
2.82
2.45
143.5
153.9
H2NH...O(CH3)2 (59)
-3.12
-3.43
-0.31
3.00
3.00
0.00
2.32
1.97
155.9
173.9
Methylammonium...OH2 (60)
-19.30
-21.17
-1.87
2.70
2.62
-0.08
1.79
1.57
173.8
176.7
Guanidinium...OHH (61)
-18.48
-19.02
-0.54
2.85
2.85
2.78
2.78
-0.07
-0.07
2.08
2.08
1.87
1.87
147.7
147.7
146.8
146.8
Imidazolium...OH2 (62)
-16.95
-17.60
-0.65
2.71
2.62
-0.08
1.81
1.59
174.5
173.4
Formamidinium...OH2 (63)
-16.98
-18.75
-1.77
2.71
2.61
-0.10
1.91
1.57
148.7
177.2
Formamidinium...OH2, cyclic C2v (64)
-19.59
-19.71
-0.12
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
Formaldehydeiminium...OH2 (65)
-19.98
-21.65
-1.67
2.83
2.66
2.78
2.65
-0.05
-0.01
2.09
1.78
1.89
1.61
142.6
163.4
143.6
176.6
OHH...(-)O2CCH3, bidentate (66)
-21.85
-22.62
-0.77
2.77
2.78
2.74
2.74
-0.03
-0.03
2.06
2.08
1.87
1.87
142.9
141.8
145.7
145.7
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-5.40
1.07
2.73
2.90
0.17
2.03
1.93
172.3
169.6
HOH...HOH, cyclic Cs (2)
-5.02
-4.26
0.76
2.58
2.88
0.30
2.31
2.25
111.8
121.4
2.58
2.88
0.30
2.31
2.25
111.8
121.4
HOH...OHCH3 (3)
-6.10
-4.61
1.49
2.72
2.93
0.22
2.01
1.97
169.0
168.1
CH3OH...OH2 (4)
-6.15
-6.53
-0.38
2.72
2.84
0.11
2.01
1.86
174.9
179.0
CH3OH...OHCH3 (5)
-6.09
-5.65
0.44
2.71
2.86
0.15
2.00
1.89
174.6
179.0
HOH...O(CH3)2 (6)
-5.84
-2.93
2.91
2.71
3.08
0.37
2.02
2.11
163.9
176.3
C6H5OH...OH2 (7)
-8.10
-6.28
1.82
2.67
2.88
0.21
1.95
1.91
174.0
173.8
HOH...OHC6H5 (8)
-5.18
-3.97
1.21
2.79
3.03
0.24
2.12
2.10
160.8
159.3
t-Vinyl alcohol...OH2 (9)
-8.18
-6.32
1.86
2.65
2.85
0.19
1.93
1.87
175.0
179.3
HOH...t-Vinyl alcohol (10)
-5.16
-5.37
-0.21
2.79
2.90
0.12
2.11
1.96
163.2
162.1
HOH...Furan (11)
-4.00
-3.86
0.14
2.78
3.14
0.36
2.22
2.22
141.6
156.6
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-10.57
6.53
2.57
2.57
2.88
2.88
0.31
0.31
1.83
1.83
1.91
1.91
175.9
175.9
169.0
169.0
H3CCOOH...OHH (13)
-10.94
-9.00
1.94
2.58
2.61
2.80
3.03
0.22
0.42
1.90
2.15
1.83
2.48
156.3
127.9
168.3
115.5
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-8.97
2.26
2.54
2.61
2.80
2.88
0.26
0.27
1.80
2.22
1.84
2.29
171.5
122.2
167.3
118.3
-4.90
-4.20
0.70
2.97
2.96
3.16
3.03
0.19
0.07
2.44
2.35
2.21
2.78
141.1
151.7
163.8
95.3
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-3.82
0.00
2.90
3.21
3.05
3.22
0.15
0.01
2.27
2.95
2.27
2.42
155.0
117.5
136.5
139.4
HOH...skew-Methyl vinyl ether (17)
-5.20
-3.78
1.42
2.73
3.03
0.30
2.08
2.09
155.6
160.8
HOH...Methyl formate (=O) (18)
-6.39
-4.58
1.81
2.76
2.98
0.22
2.06
2.00
167.0
179.2
HOH...Methyl formate (-O-) (19)
-3.82
-4.58
-0.76
2.78
4.30
1.52
2.24
3.49
138.7
141.3
HOH...Formaldehyde (20)
-5.81
-3.85
1.96
2.72
2.98
0.27
2.11
2.03
147.6
166.8
HOH...Acetone (21)
-6.87
-4.13
2.74
2.74
2.99
0.25
2.06
2.01
163.1
179.9
t-NMA...OH2 (22)
-5.97
-7.41
-1.44
2.87
2.91
0.04
2.12
1.89
178.3
179.1
HOH...t-NMA (23)
-8.03
-5.67
2.36
2.70
2.95
0.25
2.00
1.98
167.6
172.2
-14.78
-10.02
4.76
2.76
2.76
2.99
2.99
0.23
0.23
2.00
2.00
1.97
1.97
171.6
171.5
177.5
177.5
Formamide dimer, parallel (25)
-8.12
-6.49
1.63
2.80
2.98
0.19
2.09
2.06
156.7
149.8
t-NMA dimer, antiparallel (26)
-7.70
-7.88
-0.18
2.83
2.95
0.12
2.08
1.95
171.8
167.4
t-NMA antiparallel stacked (27)
-3.86
-5.28
-1.42
3.65
3.67
3.84
3.84
0.19
0.17
3.88
3.88
3.69
3.69
87.9
88.9
91.1
91.1
HOH...N-Methylformamide (28)
-7.90
-5.66
2.23
2.71
2.95
0.24
2.01
1.98
164.7
172.1
N-Methylformamide...OH2 (29)
-6.05
-7.43
-1.38
2.84
2.90
0.06
2.09
1.88
173.8
177.0
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-7.50
0.71
2.62
2.82
0.20
1.94
1.88
159.2
160.3
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-8.29
-4.19
2.82
2.82
0.01
2.12
3.49
168.7
40.3
H2NH...HNH2, cyclic C2h (32)
-3.51
-1.29
2.22
3.01
3.01
3.16
3.16
0.15
0.15
2.60
2.61
2.42
2.42
123.9
123.8
130.0
130.0
H2NH...NH3, linear Cs (33)
-3.38
-1.38
2.00
3.15
3.15
3.20
3.20
0.05
0.05
2.42
3.64
2.19
3.25
179.0
69.8
177.7
78.4
HOH...NH3 (34)
-7.22
-3.75
3.47
2.80
2.97
0.18
2.09
2.00
176.4
173.6
HOH...NH2CH3 (35)
-7.07
-3.58
3.50
2.80
3.04
0.24
2.09
2.08
175.9
169.3
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.81
-0.81
2.79
2.85
0.06
2.03
1.82
178.2
178.0
HOH...Imidazole (37)
-7.77
-6.05
1.72
2.73
3.14
0.41
2.10
2.25
151.2
150.0
Indole...OH2 (38)
-6.33
-6.82
-0.49
2.81
2.88
0.07
2.07
1.84
168.3
175.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.89
0.07
2.07
1.85
180.0
180.0
HOH...Pyridine (40)
-6.63
-4.25
2.38
2.77
3.20
0.42
2.12
2.32
155.8
148.8
Formamidine...H2O, cyclic (41)
-11.03
-8.51
2.52
2.81
2.70
2.98
2.90
0.17
0.20
2.20
2.06
2.11
1.92
143.3
151.4
142.5
171.2
HOH...Formaldehydeimine (42)
-6.74
-5.91
0.83
2.76
2.90
0.14
2.11
1.92
154.0
179.6
Guanidine...OHH (43)
-7.96
-7.00
0.96
2.88
2.77
3.01
2.97
0.13
0.20
2.25
2.21
2.10
2.06
145.4
141.1
148.2
152.8
Vinylamine...OH2 (44)
-3.80
-4.33
-0.53
3.04
2.98
-0.06
2.19
1.97
164.2
177.0
Aniline...OH2 (45)
-4.62
-5.17
-0.55
2.94
2.93
-0.01
2.20
1.91
173.2
175.0
HSH...OH2 (46)
-2.93
-2.19
0.74
3.33
3.58
0.25
2.29
2.84
175.3
113.4
HOH...S(CH3)2 (47)
-3.56
-2.05
1.51
3.12
3.12
3.28
3.28
0.16
0.16
3.13
3.13
2.30
3.64
97.7
97.7
178.2
60.6
OHH...CH3SSCH3, cyclic (48)
-3.78
-1.71
2.07
3.38
3.47
0.09
2.84
2.50
147.0
172.9
HOH...Thiophene (49)
-2.66
-4.36
-1.70
3.59
3.59
3.63
3.63
0.04
0.04
3.50
3.33
3.57
2.91
108.4
121.0
85.7
131.4
HOH...SHC6H5 (50)
-2.20
-4.38
-2.18
4.56
4.40
-0.16
4.27
3.77
132.4
125.0
HSH...SH2 (51)
-0.96
-1.23
-0.26
4.15
3.77
-0.38
3.19
3.02
175.5
114.4
HOH...SH2 (52)
-2.27
-2.75
-0.48
3.47
3.09
-0.38
2.83
2.13
175.5
167.5
CH3COOH...NH3, bidentate (53)
-11.94
-6.04
5.90
2.63
2.89
2.86
3.27
0.23
0.37
1.90
2.53
1.88
2.74
168.3
119.0
177.6
112.8
HOH...PyridineN-oxide (54)
-10.69
-7.20
3.49
2.63
2.87
0.24
1.94
1.89
161.0
177.3
MethylethylamineN-oxide...OHH( 55)
-15.48
-21.09
-5.60
2.49
3.45
0.96
1.83
3.83
148.9
59.9
2.64
2.73
0.09
2.17
1.72
124.2
170.5
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.51
0.90
2.66
2.66
2.84
3.58
0.18
0.92
2.11
2.18
1.87
3.99
138.5
130.2
173.0
58.3
HOH...FCH3 (59)
-4.87
-1.69
3.17
2.70
3.09
0.39
2.06
2.13
153.9
169.7
HOH...Chloropropane (58)
-3.09
-1.09
1.99
3.34
4.43
1.10
2.82
3.81
143.5
125.0
H2NH...O(CH3)2 (59)
-3.12
-1.18
1.94
3.00
3.36
0.36
2.32
2.35
155.9
179.8
Methylammonium...OH2 (60)
-19.30
-18.81
0.49
2.70
2.74
0.04
1.79
1.74
173.8
167.9
Guanidinium...OHH (61)
-18.48
-16.40
2.08
2.85
2.85
2.96
2.96
0.11
0.11
2.08
2.08
2.02
2.02
147.7
147.7
152.4
152.4
Imidazolium...OH2 (62)
-16.95
-15.95
1.00
2.71
2.78
0.07
1.81
1.74
174.5
172.4
OHH...(-)O2CCH3, bidentate (66)
-21.85
-17.22
4.63
2.77
2.78
2.86
2.86
0.09
0.08
2.06
2.08
2.00
2.00
142.9
141.8
143.9
143.9
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.40
0.07
2.73
2.76
0.03
2.03
1.79
172.3
173.7
HOH...HOH, cyclic Cs (2)
-5.02
-4.74
0.28
2.58
2.81
0.23
2.31
2.17
111.8
122.3
2.58
2.81
0.23
2.31
2.17
111.8
122.3
HOH...OHCH3 (3)
-6.10
-4.41
1.69
2.72
2.81
0.09
2.01
1.85
169.0
168.0
CH3OH...OH2 (4)
-6.15
-6.78
-0.63
2.72
2.66
-0.06
2.01
1.68
174.9
176.0
CH3OH...OHCH3 (5)
-6.09
-5.03
1.06
2.71
2.69
-0.02
2.00
1.72
174.6
174.9
HOH...O(CH3)2 (6)
-5.84
-5.09
0.75
2.71
2.79
0.08
2.02
1.82
163.9
173.5
C6H5OH...OH2 (7)
-8.10
-7.57
0.53
2.67
2.67
0.01
1.95
1.71
174.0
169.3
HOH...OHC6H5 (8)
-5.18
-4.18
1.00
2.79
2.83
0.05
2.12
1.88
160.8
167.9
t-Vinyl alcohol...OH2 (9)
-8.18
-7.33
0.85
2.65
2.66
0.00
1.93
1.68
175.0
177.2
HOH...t-Vinyl alcohol (10)
-5.16
-4.31
0.85
2.79
2.81
0.02
2.11
1.85
163.2
167.5
HOH...Furan (11)
-4.00
-3.87
0.13
2.78
2.93
0.15
2.22
2.01
141.6
158.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-11.14
5.96
2.57
2.57
2.66
2.66
0.09
0.09
1.83
1.83
1.70
1.70
175.9
175.9
171.7
171.7
H3CCOOH...OHH (13)
-10.94
-8.82
2.12
2.58
2.61
2.66
3.00
0.08
0.39
1.90
2.15
1.70
2.40
156.3
127.9
168.5
119.5
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.31
1.92
2.54
2.61
2.65
2.74
0.11
0.13
1.80
2.22
1.68
2.05
171.5
122.2
170.4
126.9
-4.90
-4.24
0.66
2.97
2.96
3.52
2.80
0.55
-0.15
2.44
2.35
3.02
1.83
141.1
151.7
113.9
177.7
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.31
-5.49
2.90
3.21
2.74
4.83
-0.16
1.62
2.27
2.95
2.05
5.72
155.0
117.5
126.9
21.0
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.85
0.36
2.73
2.79
0.06
2.08
1.84
155.6
165.6
HOH...Methyl formate (=O) (18)
-6.39
-6.19
0.20
2.76
2.75
-0.01
2.06
1.77
167.0
176.7
HOH...Methyl formate (-O-) (19)
-3.82
-3.20
0.62
2.78
4.04
1.27
2.24
4.34
138.7
65.9
HOH...Formaldehyde (20)
-5.81
-6.01
-0.20
2.72
2.75
0.03
2.11
1.78
147.6
174.5
HOH...Acetone (21)
-6.87
-5.30
1.57
2.74
2.76
0.02
2.06
1.79
163.1
179.2
t-NMA...OH2 (22)
-5.97
-4.19
1.78
2.87
3.07
0.20
2.12
2.04
178.3
176.8
HOH...t-NMA (23)
-8.03
-6.80
1.23
2.70
2.74
0.04
2.00
1.77
167.6
175.6
-14.78
-6.53
8.25
2.76
2.76
3.00
3.00
0.24
0.24
2.00
2.00
1.97
1.97
171.6
171.5
175.9
175.9
Formamide dimer, parallel (25)
-8.12
-5.23
2.89
2.80
3.08
0.29
2.09
2.28
156.7
133.4
t-NMA dimer, antiparallel (26)
-7.70
-5.69
2.01
2.83
3.02
0.19
2.08
2.00
171.8
168.8
t-NMA antiparallel stacked (27)
-3.86
-4.84
-0.98
3.65
3.67
4.00
4.00
0.35
0.33
3.88
3.88
3.82
3.82
87.9
88.9
92.7
92.7
HOH...N-Methylformamide (28)
-7.90
-7.18
0.72
2.71
2.73
0.02
2.01
1.76
164.7
172.1
N-Methylformamide...OH2 (29)
-6.05
-4.46
1.59
2.84
3.05
0.21
2.09
2.02
173.8
169.3
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.40
-0.19
2.62
2.64
0.02
1.94
1.68
159.2
168.0
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-9.06
-4.97
2.82
2.65
-0.17
2.12
3.31
168.7
40.6
H2NH...HNH2, cyclic C2h (32)
-3.51
-0.46
3.05
3.01
3.01
3.69
3.69
0.69
0.69
2.60
2.61
2.92
2.92
123.9
123.8
132.8
132.8
H2NH...NH3, linear Cs (33)
-3.38
-0.50
2.88
3.15
3.15
3.69
3.69
0.53
0.53
2.42
3.64
2.66
3.80
179.0
69.8
176.0
76.0
HOH...NH3 (34)
-7.22
-1.99
5.23
2.80
3.18
0.39
2.09
2.22
176.4
173.1
HOH...NH2CH3 (35)
-7.07
-4.05
3.02
2.80
3.07
0.27
2.09
2.10
175.9
178.7
Formamide dimer, cyclic (24)
Indole...OH2 (38)
-6.33
-2.59
3.74
2.81
3.09
0.28
2.07
2.06
168.3
176.9
Pyrrole...OH2 (39)
-5.89
-2.28
3.61
2.82
3.11
0.29
2.07
2.07
180.0
180.0
HOH...Pyridine (40)
-6.63
-3.36
3.27
2.77
3.48
0.70
2.12
3.26
155.8
95.0
Formamidine...H2O, cyclic (41)
-11.03
-3.49
7.54
2.81
2.70
3.21
3.18
0.40
0.48
2.20
2.06
2.28
2.25
143.3
151.4
150.4
160.8
HOH...Formaldehydeimine (42)
-6.74
-3.00
3.74
2.76
3.17
0.41
2.11
2.23
154.0
162.4
Guanidine...OHH (43)
-7.96
-5.74
2.22
2.88
2.77
3.16
3.16
0.28
0.40
2.25
2.21
2.19
3.80
145.4
141.1
157.1
42.7
Vinylamine...OH2 (44)
-3.80
-1.76
2.03
3.04
3.15
0.11
2.19
2.12
164.2
179.7
Aniline...OH2 (45)
-4.62
-2.82
1.80
2.94
3.12
0.18
2.20
2.09
173.2
179.9
HSH...OH2 (46)
-2.93
-0.98
1.95
3.33
3.48
0.15
2.29
2.94
175.3
102.6
HOH...S(CH3)2 (47)
-3.56
-1.23
2.33
3.12
3.12
3.40
3.40
0.29
0.29
3.13
3.13
3.60
2.46
97.7
97.7
70.4
166.0
OHH...CH3SSCH3, cyclic (48)
-3.78
-1.32
2.46
3.38
3.41
0.03
2.84
2.48
147.0
162.6
HOH...Thiophene (49)
-2.66
-3.76
-1.10
3.59
3.59
3.49
3.49
-0.10
-0.10
3.50
3.33
3.75
2.79
108.4
121.0
66.7
129.3
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.56
-0.01
4.27
3.99
132.4
120.4
HSH...SH2 (51)
-0.96
-0.46
0.50
4.15
3.51
-0.64
3.19
3.13
175.5
94.8
HOH...SH2 (52)
-2.27
-1.54
0.73
3.47
3.04
-0.43
2.83
2.09
175.5
171.7
CH3COOH...NH3, bidentate (53)
-11.94
-2.95
8.99
2.63
2.89
3.05
3.43
0.42
0.53
1.90
2.53
2.09
2.84
168.3
119.0
176.2
116.9
HOH...PyridineN-oxide (54)
-10.69
-3.53
7.16
2.63
3.82
1.19
1.94
4.26
161.0
57.4
MethylethylamineN-oxide...OHH( 55)
-15.48
-16.58
-1.10
2.49
2.64
3.50
2.84
1.01
0.21
1.83
2.17
3.85
1.80
148.9
124.2
62.2
174.1
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.99
0.43
2.66
2.80
0.15
2.11
2.03
138.5
135.8
2.66
2.97
0.31
2.18
2.08
130.2
151.5
HOH...FCH3 (59)
-4.87
-3.91
0.96
2.70
2.81
0.10
2.06
1.84
153.9
175.5
HOH...Chloropropane (58)
-3.09
-3.16
-0.08
3.34
3.09
-0.25
2.82
2.12
143.5
178.1
H2NH...O(CH3)2 (59)
-3.12
-1.44
1.68
3.00
3.29
0.29
2.32
2.27
155.9
177.7
Methylammonium...OH2 (60)
-19.30
-17.49
1.81
2.70
2.81
0.11
1.79
1.76
173.8
177.2
Guanidinium...OHH (61)
-18.48
-5.50
12.98
2.85
2.85
3.20
3.53
0.34
0.68
2.08
2.08
3.48
3.76
147.7
147.7
65.9
69.1
Imidazolium...OH2 (62)
-16.95
-13.21
3.74
2.71
2.86
0.16
1.81
1.82
174.5
175.5
Formamidinium...OH2 (63)
-16.98
-2.40
14.58
2.71
3.11
0.41
1.91
2.08
148.7
179.3
Formamidinium...OH2, cyclic C2v (64)
-19.59
-3.20
16.39
2.83
3.24
0.40
2.09
2.24
142.6
162.5
2.83
3.24
0.40
2.09
2.24
142.6
162.5
2.77
2.78
2.69
2.69
-0.07
-0.08
2.06
2.08
1.81
1.81
142.9
141.8
147.2
147.2
OHH...(-)O2CCH3, bidentate (66)
a
-21.85
-22.84
-0.99
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.83
-0.36
2.73
2.76
0.02
2.03
1.78
172.3
173.3
HOH...HOH, cyclic Cs (2)
-5.02
-6.75
-1.73
2.58
2.76
0.18
2.31
1.78
111.8
177.5
2.58
2.76
0.18
2.31
3.21
111.8
53.9
HOH...OHCH3 (3)
-6.10
-6.24
-0.14
2.72
2.87
0.16
2.01
1.99
169.0
151.9
CH3OH...OH2 (4)
-6.15
-5.19
0.96
2.72
2.97
0.25
2.01
2.02
174.9
171.7
CH3OH...OHCH3 (5)
-6.09
-6.49
-0.39
2.71
2.77
0.06
2.00
1.84
174.6
163.0
HOH...O(CH3)2 (6)
-5.84
-4.59
1.25
2.71
2.93
0.22
2.02
2.10
163.9
142.7
C6H5OH...OH2 (7)
-8.10
-5.66
2.44
2.67
2.98
0.31
1.95
2.03
174.0
179.5
HOH...OHC6H5 (8)
-5.18
-6.75
-1.57
2.79
2.87
0.08
2.12
2.00
160.8
150.2
t-Vinyl alcohol...OH2 (9)
-8.18
-6.25
1.93
2.65
2.95
0.29
1.93
1.99
175.0
179.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.06
0.10
2.79
2.87
0.08
2.11
2.15
163.2
130.4
HOH...Furan (11)
-4.00
-3.36
0.64
2.78
3.25
0.46
2.22
2.78
141.6
110.9
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-3.56
13.54
2.57
2.57
2.89
2.89
0.32
0.32
1.83
1.83
1.94
1.94
175.9
175.9
170.4
170.4
H3CCOOH...OHH (13)
-10.94
-6.30
4.64
2.58
2.61
3.22
2.82
0.64
0.21
1.90
2.15
2.40
1.99
156.3
127.9
144.0
143.4
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-4.15
7.08
2.54
2.61
3.16
2.74
0.62
0.12
1.80
2.22
2.21
1.96
171.5
122.2
174.9
135.6
-4.90
-7.25
-2.35
2.97
2.96
2.94
2.80
-0.03
-0.15
2.44
2.35
2.05
2.70
141.1
151.7
154.5
85.9
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-6.61
-2.79
2.90
3.21
2.84
2.91
-0.06
-0.30
2.27
2.95
2.07
2.09
155.0
117.5
136.2
141.9
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.79
0.41
2.73
2.90
0.17
2.08
2.13
155.6
135.7
HOH...Methyl formate (=O) (18)
-6.39
-7.47
-1.08
2.76
2.90
0.14
2.06
1.97
167.0
162.0
HOH...Methyl formate (-O-) (19)
-3.82
-5.68
-1.86
2.78
2.96
0.19
2.24
2.06
138.7
154.8
HOH...Formaldehyde (20)
-5.81
-5.59
0.22
2.72
2.88
0.16
2.11
2.02
147.6
148.0
HOH...Acetone (21)
-6.87
-6.18
0.70
2.74
2.91
0.17
2.06
1.98
163.1
161.1
t-NMA...OH2 (22)
-5.97
-5.20
0.77
2.87
3.11
0.25
2.12
2.11
178.3
179.3
HOH...t-NMA (23)
-8.03
-6.87
1.16
2.70
2.90
0.20
2.00
1.99
167.6
158.0
-14.78
-11.68
3.11
2.76
2.76
2.91
2.91
0.15
0.15
2.00
2.00
1.90
1.90
171.6
171.5
176.2
176.2
Formamide dimer, parallel (25)
-8.12
-8.38
-0.26
2.80
2.85
0.05
2.09
1.95
156.7
147.1
t-NMA dimer, antiparallel (26)
-7.70
-7.83
-0.13
2.83
2.82
-0.01
2.08
1.97
171.8
140.6
t-NMA antiparallel stacked (27)
-3.86
-8.08
-4.22
3.65
3.67
3.39
3.39
-0.26
-0.28
3.88
3.88
3.55
3.55
87.9
88.9
72.8
72.8
HOH...N-Methylformamide (28)
-7.90
-6.81
1.09
2.71
2.96
0.26
2.01
2.01
164.7
173.0
N-Methylformamide...OH2 (29)
-6.05
-5.39
0.66
2.84
3.08
0.24
2.09
2.08
173.8
177.0
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.21
0.00
2.62
2.90
0.28
1.94
2.08
159.2
143.6
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-8.21
-4.11
2.82
2.90
0.09
2.12
3.46
168.7
48.2
H2NH...HNH2, cyclic C2h (32)
-3.51
-5.60
-2.09
3.01
3.01
2.75
2.75
-0.26
-0.26
2.60
2.61
2.03
2.03
123.9
123.8
125.8
125.8
H2NH...NH3, linear Cs (33)
-3.38
-4.52
-1.14
3.15
3.15
2.75
2.75
-0.40
-0.40
2.42
3.64
2.03
2.03
179.0
69.8
125.8
125.8
HOH...NH3 (34)
-7.22
-6.39
0.82
2.80
2.96
0.16
2.09
2.02
176.4
162.9
HOH...NH2CH3 (35)
-7.07
-2.43
4.65
2.80
3.15
0.36
2.09
2.26
175.9
155.6
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-10.83
-3.83
2.79
2.94
0.15
2.03
1.96
178.2
176.0
HOH...Imidazole (37)
-7.77
-7.42
0.35
2.73
2.81
0.08
2.10
2.32
151.2
111.4
Indole...OH2 (38)
-6.33
-5.31
1.01
2.81
3.04
0.24
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*
OPLS*
MM2*
MM3*
N-methylformamide, cis - trans
1.03
1.09
1.28
1.83
3.44#
1.57
0.41
0.46
1.50
N-methylactamide, cis - trans
1.90
1.97
2.18
3.09
2.46
2.33
1.98
1.74
2.31
N-formylformamide,
o=c-n-h cis,trans - cis,cis
0.41
0.44
0.40
0.95
2.68#
0.37
-0.98
-1.10#
1.72
glycine dipeptide analog, C5 - C7
0.91
1.08
1.14
-0.16
2.13
1.29
0.37
5.24##
0.65
alanine dipeptide analog, C5 - C7eq
1.08
1.11
1.12
0.76
2.58#
1.68
1.69
5.52##
0.00
alanine dipeptide analog, C7ax - C7eq
2.20
1.58
1.83
1.43
1.43
1.72
2.98
1.36
1.16
alanine dipeptide analog, '- C7eq
4.88
5.24
4.85
4.54
7.04#
6.22
4.32
---
3.60
alanine dipeptide analog, 2' - C7eq
2.76
---
2.47
---
---
---
1.84
---
---
alanine dipeptide analog, L - C7eq
4.10
4.28
3.87
---
---
---
---
---
1.16#
N-OH,N-methylacetamide,
o-n-c=o cis - trans
0.04
-0.19
0.01
1.95#
---
---
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]
0.24
0.53
0.14
-1.97#
2.55#
---
---
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]
1.50
---
1.56
-2.39##
---
---
9.32##
---
---
N-OH,N-Et acetamide,
[o-n-c=o cis, c-c-n-c(=o) sk] -
0.08
---
0.27
---
0.04
---
---
---
---
Conformational comparison
Amides:
-5.40## -5.03## -9.38##
4.81## 10.08##
[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]
0.04
0.24
0.08
-2.21#
3.82##
5.17##
9.46##
---
---
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
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]
0.96
1.24
1.07
-2.41##
3.42#
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]
0.72
1.24
1.09
0.26
0.26
---
glycine dipeptide, C5 - C7
1.66
1.40
1.62
1.08
2.55
alanine dipeptide, C5 - C7eq
1.64
1.42
1.68
1.79
alanine dipeptide, C7ax - C7eq
2.20
1.84
2.26
alanine dipeptide, ' - C7eq
5.35
5.66
alanine dipeptide, 2 - C7eq
3.20
alanine dipeptide, L - C7eq
Conformational comparison
AMBER*
OPLS*
5.17## 11.29##
MM2*
MM3*
---
---
2.19
---
---
-1.20#
-0.70#
5.65##
1.25
2.93
-0.69#
0.44
6.05##
0.56
1.17
1.84
2.19
2.95
1.53
1.34
5.47
5.34
7.30#
---
5.48
---
4.26
---
3.06
---
---
---
---
---
---
4.25
4.74
4.75
---
---
---
---
---
---
formic acid, trans - cis
4.79
4.89
4.89
4.48
5.97
6.55#
7.64#
11.38##
4.89
acetic acid, trans - cis
5.86
5.87
5.87
6.05
4.76
7.23
6.67
13.66##
5.70
propanoic acid, c-c-c=o sk - cis
0.85
0.84
0.84
0.90
0.80
-0.22
-0.10
0.52
0.71
gyloxylic acid,
[o=c-c=o trans, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
0.35
1.91#
1.91#
2.94#
0.89
1.07
glycolic acid, o=c-c-o sk - cis
1.64
0.80
0.80
2.57
-2.76## -0.71#
-3.50##
propenoic acid, c=c-c=o trans - cis
0.21
0.25
0.25
0.70
-0.39
-0.14
oxalic acid,
[o=c-c=o trans, o=c-o-h cis,cis] -
2.22
0.97
0.97
6.22##
7.46##
Carboxylic Acids:
-0.03
0.01#
5.08## -5.68## -0.49
0.94
2.88
-0.05
-1.17
9.84## -8.85## -1.74##
[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]
1.65
1.90
1.90
3.94##
4.05##
1.34
6.30## -2.61## -0.34#
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
1.67
2.42
2.42
2.97
2.48
1.52
4.42#
methyl formate, o=c-o-c trans - cis
5.65
5.28
5.28
5.09
5.54
1.34##
0.87##
5.61
2.18##
methyl acetate, o=c-o-c trans - cis
vinyl formate, c=c-o-c cis - trans
8.21
8.27
8.27
8.67
9.09
7.42
7.47
6.68#
7.85
ethyl formate, c-o-c-c g - a
2.79
2.83
2.83
---
4.79#
---
---
2.84
---
0.34
0.44
0.44
0.67
---
0.99
0.69
0.27
0.23
isopropyl formate, c-c-o-c g,g - g,a
2.43
2.43
2.43
2.16
5.58##
2.65
2.84
0.74#
1.60
phenyl acetate, o=c-o-c cis - trans
4.30
4.50
4.50
2.58#
1.32#
2.06#
4.93
8.80##
1.28##
methyl glycolate, o=c-c-o sk - cis
1.48
2.43
2.43
2.40
-3.25##
0.35
-0.03#
2.22
2.84
1,3-butadiene, g - s-trans
2.39
2.46
2.46
3.39
2.39
2.45
2.80
2.74
1.72
2-methyl-1,3-butadiene, g - s-trans
2.20
2.12
2.12
2.79
1.95
3.29
1.85
2.49
1.63
2-methyl-but-1-ene-3-one,
c=c-c=o cis - trans
2.08
1.90
1.90
-0.42#
2.46
-0.57#
1.37
1.66
1.95
2-methylpropenamide, c=c-c=o cis - sk
1.05
1.04
1.00
-0.42
6.08## -3.13##
0.16
2.90#
1.04
propenamide, c=c-c=o sk - cis
0.61
0.57
0.60
0.31
but-1-ene-3-one, c=c-c=o cis - trans
0.43
0.28
0.28
0.69
0.58
acrolein, c=c-c=o cis - trans
2.03
2.05
2.05
1.59
2-methylpropenal, c=c-c=o cis - trans
3.14
3.15
3.15
-0.07##
Conformational comparison
pyruvic acid,
[o=c-c=o cis, o=c-o-h cis] [o=c-c=o trans, o=c-o-h trans]
MM2*
MM3*
-4.13## -0.16#
Esters:
Congujated systems:
-3.02## -1.77#
-2.26#
-0.84
-0.79
0.67
1.43
0.50
0.71
2.47
2.03
1.69
1.64
1.98
5.50#
1.40#
0.64#
3.25
3.46
2-methylpropenoic acid,
c=c-c=o cis - trans
0.60
0.62
0.62
-0.45
0.71
-0.52
0.38
-1.18#
1.30
1,3-pentadiene,
[c=c-c=c g, c-c=c-c trans] [c=c-c=c s-trans, c-c=c-c trans]
2.43
2.46
2.46
3.24
2.56
2.70
3.19
2.83
1.83
"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
propionaldehyde, c-c-c=o sk - cis
0.83
0.53
0.53
1.09
0.32
1.65
-0.46
0.90
1.10
2-butanone c-c-c=o sk - cis
0.98
0.83
0.83
1.35
0.19
1.73
-0.04
1.57
1.61
methyl ispropyl ketone,
o=c-c(ch3)2-h cis - trans
0.69
0.89
0.89
1.24
0.87
1.65
0.40
1.36
1.53
butyraldehyde, c-c-c-c g - a
0.14
0.11
0.11
0.87
0.89
1.27
1.08
0.84
0.91
but-3-enal,
[c=c-c-c sk, c-c-c=o cis] [c=c-c-c sk+, c-c-c=o sk+]
0.20
-0.05
-0.05
---
1.16
-0.96
-0.11
0.95
2.11#
but-3-enal,
[c=c-c-c sk-, c-c-c=o sk+] [c=c-c-c sk+, c-c-c=o sk+]
0.29
0.98
0.98
0.65
0.71
0.51
0.62
0.07
0.51
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]
0.43
0.72
0.72
0.06
1.34
0.08
1.31
1.25
2.68#
isobutyraldehyde, h-c(=0)-c-h a - g
0.37
0.56
0.56
0.97
0.04
1.58
-0.49
0.99
1.16
2-formylpropanal, o-c-c-c(=o) a - g
0.18
0.14
0.14
0.01
-1.94#
0.25
-0.33
4-oxobutanal (o=c-c-c, c-c-c=o cis, cis),
c-c-c-c s-trans - g
0.70
0.77
0.77
-1.34#
-0.98#
2.14
0.03
-0.24
-1.37#
2,3-butanedione, c-c-c-c g - s-trans
5.40
---
---
3.51#
4.66
---
---
Conformational comparison
1,3-pentadiene,
[s-trans, c-c=c-c cis] [s-trans, c-c=c-c trans]
Aldehydes and ketones:
-3.85## -2.60#
7.12#
2.88#
Halides:
1,2-difluoroethane, a - g
0.58
0.63
0.63
-1.57#
1.05
-1.16#
-0.93#
0.01
0.04
1,2-dicloroethane, g - a
1.29
1.24
1.24
1.22
1.47
1.13
0.87
1.13
1.95
1-fluoropropane, a - g
0.03
0.06
0.06
-0.93
-0.12
0.03
-0.41
-0.08
-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
formamidine (N puckered),
h-n=c-n cis - trans
2.03
2.03
2.27
1.62
2.08
1.78
4.23#
-0.96#
-0.68#
N-methylformamidine (N puckered),
n-c=n-c cis - trans
2.00
2.00
2.12
2.67
-3.12##
3.82#
---
-0.09#
1.03
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]
1.73
1.94
1.94
6.58##
2.63
1.96
1.89
2.60
1.99
2-methoxytetrahydropyran,
[eq, me-o-c-c a] - [ax, me-o-c-c a]
1.30
1.81
1.81
1.88
2.37
0.97
1.70
2.27
1.63
2,4-dioxapentane,
[c-o-c-o g, o-c-o-c a] [c-o-c-o g+, o-c-o-c g+]
2.44
2.11
2.11
2.54
3.37
2.95
1.93
2.99
2.26
2,5-dimethyl-1,3-dioxane, 5-ax - 5-eq
0.63
0.50
0.50
0.04
-0.65
-0.67
0.41
0.69
0.75
methoxymethanol,
[c-o-c-o g+, o-c-o-h g-] [c-o-c-o g+, o-c-o-h g+]
2.25
2.97
2.97
1.96
-3.98##
2.34
2.86
2.84
2.94
N-proplyamine cation, c-c-c-n g - a
0.07
0.03
0.03
0.29
-0.32
-0.65
0.34
0.99
1.12
ethylguanidine cation, c-c-n=c g - a
0.62
0.38
0.38
---
-1.37#
-0.18
0.33
0.11
---
Conformational comparison
1-chloropropane, g - a
Imines, guanidines, and amidines
Ketals, acetals, and hemiacetals:
Cations:
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
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
isopropylamine,
[C1, h-c-n-lp g] [Cs, h-c-n-lp a]
0.50
0.45
0.45
0.16
-0.07
0.23
0.00
0.15
0.22
cyclohexylamine, ax - eq
0.69
0.67
0.67
0.83
1.78
-0.74
0.62
1.38
1.23
piperidine, n-h ax - eq
0.78
0.90
0.90
0.05
0.13
0.14
-0.04
0.31
0.31
N-methylpiperidine, ax - eq
3.58
3.28
3.28
3.25
2.70
1.26#
2.32
2.53
2.31
ethylamine, c-c-n-lp a - g
0.08
0.44
0.44
0.20
0.22
0.26
0.00
0.14
0.12
3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
0.50
0.51
0.51
2.44#
0.00
-0.84
-1.07#
0.71
1.82
3-aminopropene,
[c=c-c-n sk, c-c-n-lp a] [c=c-c-n sk, c-c-n-lp g]
0.15
0.65
0.65
-0.17
-0.21
-0.18
0.68
-0.30
-0.08
2-methyl,3-aminopropene,
[c=c-c-n cis, c-c-n-lp g] [c=c-c-n sk, c-c-n-lp g]
0.67
0.61
0.61
1.19
0.47
0.32
-0.93#
1.03
1.75
ethylenediamine,
[n-c-c-n a, c-c-n-lp g+, g+] [n-c-c-n g+, c-c-n-lp g+, g+]
1.39
1.45
1.45
0.84
1.48
1.20
0.59
methylethylamine N-oxide, c-n-c-c g - a
1.38
1.41
1.41
-0.73#
3.62#
1.23
---
---
---
methylethylhydroxylamine, c-n-c-c g - a
1.69
2.25
2.25
1.63
1.76
1.17
1.61
1.20
---
ethylamine N-oxide, o-n-c-c a - g
0.68
0.73
0.73
-1.61#
1.61
0.68
---
---
---
ethylhydroxylamine, o-n-c-c a - g
0.20
0.05
0.05
-0.57
2.98#
0.55
-0.28
-0.05
---
Conformational comparison
12.94## 21.84##
Alcohols:
ethanol, a - g
0.06
-0.18
-0.18
-0.37
-0.23
-0.36
0.00
-0.60
-0.41
n-propanol,
[c-c-c-o g-, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
0.23
0.58
0.58
-0.42
0.02
-0.76
0.28
0.36
0.60
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
n-propanol,
[c-c-c-o g+, c-c-o-h g+] [c-c-c-o a, c-c-o-h g]
0.05
0.24
0.24
0.01
-0.43
-0.62
0.28
0.36
0.35
n-propanol,
[c-c-c-o a, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
0.20
-0.17
-0.17
-0.49
-0.16
-0.30
0.00
-0.60
-0.42
n-propanol,
[c-c-c-o g, c-c-o-h a] [c-c-c-o a, c-c-o-h g]
0.10
0.12
0.12
-0.23
-0.29
-0.81
0.28
-0.30
-0.06
isopropanol, h-c-o-h a - g
0.20
0.17
0.17
0.40
0.02
0.25
0.00
0.61
0.68
cyclopentanol, eq Cs - ax C1
1.11
0.82
0.82
-0.27
---
-0.36
-0.07
0.40
0.89
cyclopentanol, ax Cs- ax C1
1.05
0.59
0.59
-0.33
-0.94#
---
0.00
0.82
1.35
cyclopentanol, eq C1 - ax C1
1.14
0.47
0.47
-0.53#
-0.62#
0.70
-0.07
-0.23
-0.15
cyclohexanol, eq Cs - eq C1
0.18
0.20
0.20
0.38
0.06
0.15
0.00
0.62
0.77
cyclohexanol, ax Cs - eq C1
1.14
1.01
1.01
-0.49#
0.58
-0.87#
0.50
1.46
2.43
cylohexanol, ax C1 - eq C1
0.33
0.32
0.32
0.24
0.40
-0.57
0.50
0.58
0.74
vinyl alcohol, c=c-o-h trans - sk
1.43
1.43
1.43
1.58
0.66
-0.81#
-0.69#
1.75
-0.09#
benzyl alcohol, h-o-c-c a - g
1.13
1.59
1.59
1.38
2.97#
0.81
1.23
1.22
1.33
propen-3-ol,
[c=c-c-o sk, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
1.24
1.10
1.10
0.82
2.43
1.07
0.19
1.20
1.12
propen-3-ol,
[c=c-c-o cis, c-c-o-h a] [c=c-c-o sk, c-c-o-h g]
1.11
1.13
1.13
3.39#
0.49
-0.08
-1.06#
0.83
2.76#
Conformational comparison
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]
0.38
0.47
0.47
0.94
0.39
-0.71
-1.57#
-0.10
1.53
sec-butanol, ga/ga - ga/aga
0.10
0.33
0.33
-0.62
0.23
-0.30
0.00
0.07
0.24
sec-butanol, ga/gg - ga/ag
0.18
0.11
0.11
0.23
-0.32
0.05
0.00
0.64
0.69
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
sec-butanol, ag/ag - ga/ag
0.48
0.47
0.47
0.57
1.02
0.93
0.71
0.53
0.49
sec-butanol, ag/ga - ga/ag
0.29
0.46
0.46
0.74
1.06
0.85
0.71
0.53
0.50
sec-butanol, ag/gg - ga/ag
0.56
0.59
0.59
1.15
0.87
1.07
0.71
1.14
1.14
sec-butanol, gg/ag - ga/ag
0.75
0.72
0.72
0.87
0.79
0.40
1.00
0.82
0.98
sec-butanol, gg/ga - ga/ag
0.57
0.66
0.66
0.68
0.43
0.20
1.00
0.90
0.97
sec-butaone, gg/gg - ga/ag
1.13
1.14
1.14
0.56
1.01
0.33
1.00
1.54
2.06
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]
2.71
2.91
2.91
0.70#
2.45
5.69#
17.30##
2.30
0.80#
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]
0.49
1.15
1.15
1.45
0.79
0.29
---
1.47
---
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]
1.41
1.58
1.58
1.92
1.17
0.37
---
1.50
---
methyl ethyl ether, g - a
1.41
1.50
1.50
1.46
1.53
1.79
1.85
1.74
1.48
methyl vinyl ether, c=c-o-c skew - cis
2.27
2.22
2.22
-3.10##
2.10
1.07
0.60#
diethyl ether,
[c-c-o-c a, c-o-c-c g] [c-c-o-c a, c-o-c-c a]
1.48
1.52
1.52
1.37
1.55
1.83
1.84
1.77
1.49
methoxycyclohexane, eq Cs - ax C1
2.10
1.95
1.95
2.19
1.56
2.76
2.08
1.53
1.80
methoxycyclohexane, eq C1 - ax C1
0.01
-0.41
-0.41
0.11
-0.70
0.34
-0.37
-0.56
-0.76
Conformational comparison
Ethers:
-2.90## -3.94##
methyl isopropyl ether, h-c-o-ch3 a - g
1.91
1.88
1.88
2.10
1.91
2.25
2.20
1.73
2.12
0.65
0.78
0.78
0.89
0.78
0.39
0.95
0.86
0.81
Alkanes:
butane, g - a
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
cyclohexane, twist-boat - chair
6.14
5.93
5.93
7.08
6.72
5.79
6.77
5.36
5.76
methylcyclohexane, ax - eq
1.69
1.37
1.37
1.84
1.80
0.90
1.78
1.78
1.77
2,3-dimethylbutane, h-c2-c3-h g - a
0.04
-0.23
-0.23
0.13
0.40
-0.22
-0.48
0.15
0.38
cyclooctane, D4d crown - Cs boat-chair
2.00
1.44
1.44
1.21
0.45#
0.83
-1.67##
0.96
1.12
cyclooctane,
C2 twist-boat-chair - Cs boat-chair
1.71
1.99
1.99
2.30
1.88
1.77
1.20
1.66
1.85
cyclooctane, S4 - Cs boat-chair
2.97
3.27
3.27
0.16#
4.48#
3.63
6.51##
3.12
2.62
methylcyclobutane, ax - eq
0.77
0.78
0.78
1.21
0.06
0.17
0.63
0.58
0.92
cyclononane, C2 [144] - D3 [333]
1.97
1.41
1.41
1.02
0.37#
0.53
-1.02#
0.77
1.15
cyclononane, C2 [225] - D3 [333]
0.99
1.21
1.21
-1.63#
1.12
1.07
0.80
0.75
0.84
cyclononane, C1 [234] - D3 [333]
3.65
3.81
3.81
2.03#
3.45
3.66
4.31
3.16
3.04
1-butene, c=c-c-c cis - sk
0.26
0.26
0.26
0.72
0.46
0.66
1.00
0.49
0.68
1-pentene (c=c-c-c skew),
c-c-c-c g - a
0.61
0.51
0.51
0.90
-0.10
0.11
0.60
0.78
0.42
2-methyl-1-butene, c=c-c-c skew - cis
0.02
-0.03
-0.03
-0.07
-0.93
-0.97
-0.98
-0.06
-0.38
1,4-pentadiene,
c=c-c-c sk+,sk- - sk-,sk-
0.33
0.43
0.43
0.33
0.19
0.44
0.25
0.07
0.27
2-butene, cis - trans
1.27
1.35
1.35
1.43
1.61
1.55
2.49
1.43
1.02
2-pentene,
[c-c=c-c cis, c-c-c=c sk] [c-c=c-c trans, c-c-c=c sk]
1.31
1.33
1.33
1.35
1.61
1.43
2.39
1.29
0.99
Conformational comparison
Alkenes:
Thiols, sulfides, and disulfides:
ethanethiol, c-c-s-h a - g
0.74
0.68
0.68
0.33
-0.78#
-0.20
0.00
0.28
-0.04
ethyl methyl disulfide, c-c-s-s a - g
0.76
0.76
0.76
-0.31
0.11
-1.29#
0.04
-0.19
0.05
"MP4/
MMFF
MMFF
CFF
MSI
TZP"
94s
94
95
CHARMm
AMBER*
OPLS*
MM2*
MM3*
1-propanethiol,
[s-c-c-c g-, h-s-c-c g+] [s-c-c-c a, h-s-c-c g]
0.30
0.37
0.37
1.59
-0.84
1.51
0.48
0.84
1.04
1-propanethiol,
[s-c-c-c g, h-s-c-c a] [s-c-c-c a, h-s-c-c g]
1.23
0.95
0.95
2.26
-1.65#
1.53
0.48
0.92
0.65
1,2-ethanedithiol,
[all anti] [h-s-c-c a,g+, s-c-c-s g-]
0.86
1.17
1.17
0.15
-0.95#
6.92##
5.17#
-0.92#
-1.71#
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-]
1.77
2.24
2.24
1.71
0.26#
1.62
5.51##
0.68
0.34
methyl propyl sulfide,
[c-s-c-c g-, s-c-c-c g-] [c-s-c-c g, s-c-c-c a]
0.09
0.05
0.05
1.56
-0.08
1.21
0.12
0.58
0.61
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c g] [c-s-c-c g, s-c-c-c a]
0.66
0.60
0.60
-0.03
0.18
0.94
-0.24
0.24
0.51
methyl propyl sulfide,
[c-s-c-c a, s-c-c-c a] [c-s-c-c g, s-c-c-c a]
0.25
0.33
0.33
-1.66#
0.23
-0.24
-0.43
-0.39
-0.18
Conformational comparison
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.61
-0.14
2.73
2.75
0.02
2.03
1.78
172.3
170.4
HOH...HOH, cyclic Cs (2)
-5.02
-4.91
0.11
2.58
2.78
0.19
2.31
2.19
111.8
117.0
2.58
2.78
0.19
2.31
2.19
111.8
117.0
HOH...OHCH3 (3)
-6.10
-6.33
-0.23
2.72
2.73
0.02
2.01
1.76
169.0
168.7
CH3OH...OH2 (4)
-6.15
-6.15
0.00
2.72
2.75
0.03
2.01
1.76
174.9
179.9
CH3OH...OHCH3 (5)
-6.09
-6.04
0.05
2.71
2.73
0.02
2.00
1.74
174.6
177.0
HOH...O(CH3)2 (6)
-5.84
-5.98
-0.14
2.71
2.77
0.06
2.02
1.81
163.9
166.7
C6H5OH...OH2 (7)
-8.10
-8.45
-0.35
2.67
2.69
0.02
1.95
1.72
174.0
167.5
HOH...OHC6H5 (8)
-5.18
-5.08
0.10
2.79
2.83
0.04
2.12
1.89
160.8
159.9
t-Vinyl alcohol...OH2 (9)
-8.18
-8.48
-0.30
2.65
2.68
0.02
1.93
1.69
175.0
176.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.46
-0.30
2.79
2.81
0.02
2.11
1.87
163.2
160.4
HOH...Furan (11)
-4.00
-3.78
0.22
2.78
2.88
0.10
2.22
1.97
141.6
155.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-17.09
0.01
2.57
2.57
2.62
2.62
0.05
0.05
1.83
1.83
1.63
1.63
175.9
175.9
169.2
169.2
H3CCOOH...OHH (13)
-10.94
-11.70
-0.76
2.58
2.61
2.64
2.77
0.07
0.16
1.90
2.15
1.67
2.11
156.3
127.9
163.4
122.8
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
2.54
2.61
2.61
2.60
0.07
-0.02
1.80
2.22
1.61
1.92
171.5
122.2
175.4
123.9
-4.90
-6.10
-1.20
2.97
2.96
2.94
2.79
-0.04
-0.17
2.44
2.35
2.02
2.69
141.1
151.7
155.7
85.4
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
2.90
3.21
2.86
3.20
-0.04
-0.01
2.27
2.95
2.02
2.43
155.0
117.5
142.6
135.5
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.80
0.40
2.73
2.87
0.14
2.08
1.94
155.6
159.0
HOH...Methyl formate (=O) (18)
-6.39
-6.84
-0.45
2.76
2.73
-0.03
2.06
1.75
167.0
177.6
HOH...Methyl formate (-O-) (19)
-3.82
-2.62
1.20
2.78
2.95
0.17
2.24
2.12
138.7
142.0
HOH...Formaldehyde (20)
-5.81
-6.74
-0.93
2.72
2.71
0.00
2.11
1.74
147.6
170.5
HOH...Acetone (21)
-6.87
-7.06
-0.19
2.74
2.71
-0.03
2.06
1.73
163.1
173.1
t-NMA...OH2 (22)
-5.97
-6.86
-0.89
2.87
2.84
-0.03
2.12
1.82
178.3
176.9
HOH...t-NMA (23)
-8.03
-8.19
-0.16
2.70
2.71
0.00
2.00
1.73
167.6
174.2
-14.78
-12.26
2.52
2.76
2.76
2.81
2.81
0.06
0.06
2.00
2.00
1.79
1.79
171.6
171.5
173.4
173.4
Formamide dimer, parallel (25)
-8.12
-7.69
0.43
2.80
2.76
-0.03
2.09
1.74
156.7
174.4
t-NMA dimer, antiparallel (26)
-7.70
-9.08
-1.38
2.83
2.76
-0.07
2.08
1.76
171.8
165.3
t-NMA antiparallel stacked (27)
-3.86
-5.62
-1.76
3.65
3.67
3.61
3.61
-0.05
-0.06
3.88
3.88
3.49
3.49
87.9
88.9
88.5
88.4
HOH...N-Methylformamide (28)
-7.90
-8.07
-0.17
2.71
2.71
0.00
2.01
1.73
164.7
174.8
N-Methylformamide...OH2 (29)
-6.05
-6.94
-0.89
2.84
2.82
-0.01
2.09
1.80
173.8
175.4
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-7.99
0.22
2.62
2.70
0.08
1.94
1.72
159.2
175.8
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-3.95
0.15
2.82
2.85
0.03
2.12
1.87
168.7
175.8
H2NH...HNH2, cyclic C2h (32)
-3.51
-3.02
0.49
3.01
3.01
3.11
3.11
0.10
0.10
2.60
2.61
2.40
2.40
123.9
123.8
125.4
125.4
H2NH...NH3, linear Cs (33)
-3.38
-3.67
-0.29
3.15
3.15
3.03
3.03
-0.12
-0.12
2.42
3.64
2.00
3.36
179.0
69.8
178.1
62.7
HOH...NH3 (34)
-7.22
-6.83
0.39
2.80
2.80
0.00
2.09
1.82
176.4
173.9
HOH...NH2CH3 (35)
-7.07
-6.70
0.37
2.80
2.82
0.02
2.09
1.84
175.9
173.1
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.91
-0.91
2.79
2.82
0.04
2.03
1.81
178.2
175.6
HOH...Imidazole (37)
-7.77
-7.93
-0.16
2.73
2.75
0.01
2.10
1.81
151.2
158.6
Indole...OH2 (38)
-6.33
-6.51
-0.18
2.81
2.86
0.05
2.07
1.84
168.3
179.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.86
0.04
2.07
1.84
180.0
180.0
HOH...Pyridine (40)
-6.63
-7.10
-0.47
2.77
2.79
0.02
2.12
1.85
155.8
158.9
Formamidine...H2O, cyclic (41)
-11.03
-10.65
0.38
2.81
2.70
2.97
2.76
0.15
0.06
2.20
2.06
2.09
1.80
143.3
151.4
142.8
162.0
HOH...Formaldehydeimine (42)
-6.74
-7.95
-1.21
2.76
2.74
-0.02
2.11
1.77
154.0
167.6
Guanidine...OHH (43)
-7.96
-7.47
0.49
2.88
2.77
2.90
2.94
0.02
0.18
2.25
2.21
1.98
2.11
145.4
141.1
148.1
141.1
Vinylamine...OH2 (44)
-3.80
-4.61
-0.81
3.04
2.87
-0.17
2.19
1.85
164.2
173.3
Aniline...OH2 (45)
-4.62
-4.86
-0.24
2.94
2.87
-0.06
2.20
1.85
173.2
172.8
HSH...OH2 (46)
-2.93
-2.91
0.02
3.33
3.38
0.05
2.29
2.03
175.3
172.8
HOH...S(CH3)2 (47)
-3.56
-3.48
0.08
3.12
3.12
3.35
3.35
0.23
0.23
3.13
3.13
2.38
3.62
97.7
97.7
170.8
66.4
OHH...CH3SSCH3, cyclic (48)
-3.78
-3.22
0.56
3.38
3.55
0.17
2.84
2.58
147.0
174.6
HOH...Thiophene (49)
-2.66
-2.71
-0.05
3.59
3.59
3.69
3.69
0.10
0.10
3.50
3.33
3.03
3.34
108.4
121.0
126.8
103.6
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.37
-0.19
4.27
3.55
132.4
144.2
HSH...SH2 (51)
-0.96
-1.25
-0.29
4.15
4.02
-0.13
3.19
2.70
175.5
167.3
HOH...SH2 (52)
-2.27
-2.00
0.27
3.47
3.49
0.02
2.83
2.55
175.5
163.2
CH3COOH...NH3, bidentate (53)
-11.94
-11.58
0.36
2.63
2.89
2.66
3.02
0.03
0.12
1.90
2.53
1.66
2.43
168.3
119.0
174.3
115.2
HOH...PyridineN-oxide (54)
-10.69
-10.61
0.08
2.63
2.64
0.01
1.94
1.65
161.0
178.6
MethylethylamineN-oxide...OHH( 55)
-15.48
-14.87
0.61
2.49
2.59
0.10
1.83
1.66
148.9
154.6
2.64
2.74
0.11
2.17
2.10
124.2
117.6
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
2.66
2.66
2.79
2.88
0.13
0.22
2.11
2.18
1.94
2.10
138.5
130.2
143.2
135.1
HOH...FCH3 (59)
-4.87
-4.48
0.39
2.70
2.66
-0.04
2.06
1.69
153.9
172.7
HOH...Chloropropane (58)
-3.09
-2.84
0.25
3.34
3.35
0.01
2.82
2.45
143.5
153.9
H2NH...O(CH3)2 (59)
-3.12
-3.43
-0.31
3.00
3.00
0.00
2.32
1.97
155.9
173.9
Methylammonium...OH2 (60)
-19.30
-21.17
-1.87
2.70
2.62
-0.08
1.79
1.57
173.8
176.7
Guanidinium...OHH (61)
-18.48
-19.02
-0.54
2.85
2.85
2.78
2.78
-0.07
-0.07
2.08
2.08
1.87
1.87
147.7
147.7
146.8
146.8
Imidazolium...OH2 (62)
-16.95
-17.60
-0.65
2.71
2.62
-0.08
1.81
1.59
174.5
173.4
Formamidinium...OH2 (63)
-16.98
-18.75
-1.77
2.71
2.61
-0.10
1.91
1.57
148.7
177.2
Formamidinium...OH2, cyclic C2v (64)
-19.59
-19.71
-0.12
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
Formaldehydeiminium...OH2 (65)
-19.98
-21.65
-1.67
2.66
2.65
-0.01
1.78
1.61
163.4
176.6
OHH...(-)O2CCH3, bidentate (66)
-21.85
-22.62
-0.77
2.77
2.78
2.74
2.74
-0.03
-0.03
2.06
2.08
1.87
1.87
142.9
141.8
145.7
145.7
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.61
-0.14
2.73
2.75
0.02
2.03
1.78
172.3
170.4
HOH...HOH, cyclic Cs (2)
-5.02
-4.91
0.11
2.58
2.78
0.19
2.31
2.19
111.8
117.0
2.58
2.78
0.19
2.31
2.19
111.8
117.0
HOH...OHCH3 (3)
-6.10
-6.33
-0.23
2.72
2.73
0.02
2.01
1.76
169.0
168.7
CH3OH...OH2 (4)
-6.15
-6.15
0.00
2.72
2.75
0.03
2.01
1.76
174.9
179.9
CH3OH...OHCH3 (5)
-6.09
-6.04
0.05
2.71
2.73
0.02
2.00
1.74
174.6
177.0
HOH...O(CH3)2 (6)
-5.84
-5.98
-0.14
2.71
2.77
0.06
2.02
1.81
163.9
166.7
C6H5OH...OH2 (7)
-8.10
-8.45
-0.35
2.67
2.69
0.02
1.95
1.72
174.0
167.5
HOH...OHC6H5 (8)
-5.18
-5.08
0.10
2.79
2.83
0.04
2.12
1.89
160.8
159.9
t-Vinyl alcohol...OH2 (9)
-8.18
-8.48
-0.30
2.65
2.68
0.02
1.93
1.69
175.0
176.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.46
-0.30
2.79
2.81
0.02
2.11
1.87
163.2
160.4
HOH...Furan (11)
-4.00
-3.78
0.22
2.78
2.88
0.10
2.22
1.97
141.6
155.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-17.09
0.01
2.57
2.57
2.62
2.62
0.05
0.05
1.83
1.83
1.63
1.63
175.9
175.9
169.2
169.2
H3CCOOH...OHH (13)
-10.94
-11.70
-0.76
2.58
2.61
2.64
2.77
0.07
0.16
1.90
2.15
1.67
2.11
156.3
127.9
163.4
122.8
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-12.72
-1.49
2.54
2.61
2.61
2.60
0.07
-0.02
1.80
2.22
1.61
1.92
171.5
122.2
175.4
123.9
-4.90
-6.10
-1.20
2.97
2.96
2.94
2.79
-0.04
-0.17
2.44
2.35
2.02
2.69
141.1
151.7
155.7
85.4
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.67
-0.85
2.90
3.21
2.86
3.20
-0.04
-0.01
2.27
2.95
2.02
2.43
155.0
117.5
142.6
135.5
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.80
0.40
2.73
2.87
0.14
2.08
1.94
155.6
159.0
HOH...Methyl formate (=O) (18)
-6.39
-6.84
-0.45
2.76
2.73
-0.03
2.06
1.75
167.0
177.6
HOH...Methyl formate (-O-) (19)
-3.82
-2.62
1.20
2.78
2.95
0.17
2.24
2.12
138.7
142.0
HOH...Formaldehyde (20)
-5.81
-6.74
-0.93
2.72
2.71
0.00
2.11
1.74
147.6
170.5
HOH...Acetone (21)
-6.87
-7.06
-0.19
2.74
2.71
-0.03
2.06
1.73
163.1
173.1
t-NMA...OH2 (22)
-5.97
-6.87
-0.90
2.87
2.84
-0.03
2.12
1.81
178.3
179.9
HOH...t-NMA (23)
-8.03
-8.25
-0.22
2.70
2.70
0.00
2.00
1.72
167.6
174.3
-14.78
-12.26
2.52
2.76
2.76
2.81
2.81
0.06
0.06
2.00
2.00
1.79
1.79
171.6
171.5
173.4
173.4
Formamide dimer, parallel (25)
-8.12
-7.69
0.43
2.80
2.76
-0.03
2.09
1.74
156.7
174.1
t-NMA dimer, antiparallel (26)
-7.70
-9.06
-1.36
2.83
2.76
-0.07
2.08
1.75
171.8
166.8
t-NMA antiparallel stacked (27)
-3.86
-5.33
-1.47
3.65
3.67
3.64
3.64
-0.01
-0.02
3.88
3.88
3.54
3.54
87.9
88.9
88.0
88.0
HOH...N-Methylformamide (28)
-7.90
-8.14
-0.24
2.71
2.71
0.00
2.01
1.73
164.7
174.9
N-Methylformamide...OH2 (29)
-6.05
-6.90
-0.85
2.84
2.83
-0.01
2.09
1.80
173.8
175.5
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.30
-0.09
2.62
2.70
0.08
1.94
1.72
159.2
177.0
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-4.26
-0.16
2.82
2.84
0.03
2.12
1.87
168.7
178.2
H2NH...HNH2, cyclic C2h (32)
-3.51
-3.02
0.49
3.01
3.01
3.11
3.11
0.10
0.10
2.60
2.61
2.40
2.40
123.9
123.8
125.4
125.4
H2NH...NH3, linear Cs (33)
-3.38
-3.67
-0.29
3.15
3.15
3.03
3.03
-0.12
-0.12
2.42
3.64
2.00
3.36
179.0
69.8
178.1
62.7
HOH...NH3 (34)
-7.22
-6.83
0.39
2.80
2.80
0.00
2.09
1.82
176.4
173.9
HOH...NH2CH3 (35)
-7.07
-6.70
0.37
2.80
2.82
0.02
2.09
1.84
175.9
173.1
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.91
-0.91
2.79
2.82
0.04
2.03
1.81
178.2
175.6
HOH...Imidazole (37)
-7.77
-7.93
-0.16
2.73
2.75
0.01
2.10
1.81
151.2
158.6
Indole...OH2 (38)
-6.33
-6.51
-0.18
2.81
2.86
0.05
2.07
1.84
168.3
179.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.86
0.04
2.07
1.84
180.0
180.0
HOH...Pyridine (40)
-6.63
-7.10
-0.47
2.77
2.79
0.02
2.12
1.85
155.8
158.9
Formamidine...H2O, cyclic (41)
-11.03
-10.68
0.35
2.81
2.70
2.97
2.77
0.16
0.07
2.20
2.06
2.13
1.80
143.3
151.4
137.8
167.5
HOH...Formaldehydeimine (42)
-6.74
-7.95
-1.21
2.76
2.74
-0.02
2.11
1.77
154.0
167.6
Guanidine...OHH (43)
-7.96
-7.02
0.94
2.88
2.77
2.88
3.22
0.00
0.46
2.25
2.21
1.88
3.84
145.4
141.1
165.7
45.0
Vinylamine...OH2 (44)
-3.80
-4.23
-0.43
3.04
2.88
-0.16
2.19
1.85
164.2
176.9
Aniline...OH2 (45)
-4.62
-4.54
0.08
2.94
2.88
-0.06
2.20
1.86
173.2
174.9
HSH...OH2 (46)
-2.93
-2.91
0.02
3.33
3.38
0.05
2.29
2.03
175.3
172.8
HOH...S(CH3)2 (47)
-3.56
-3.48
0.08
3.12
3.12
3.35
3.35
0.23
0.23
3.13
3.13
2.38
3.62
97.7
97.7
170.8
66.4
OHH...CH3SSCH3, cyclic (48)
-3.78
-3.22
0.56
3.38
3.55
0.17
2.84
2.58
147.0
174.6
HOH...Thiophene (49)
-2.66
-2.71
-0.05
3.59
3.59
3.69
3.69
0.10
0.10
3.50
3.33
3.03
3.34
108.4
121.0
126.8
103.6
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.37
-0.19
4.27
3.55
132.4
144.2
HSH...SH2 (51)
-0.96
-1.25
-0.29
4.15
4.02
-0.13
3.19
2.70
175.5
167.3
HOH...SH2 (52)
-2.27
-2.00
0.27
3.47
3.49
0.02
2.83
2.55
175.5
163.2
CH3COOH...NH3, bidentate (53)
-11.94
-11.58
0.36
2.63
2.89
2.66
3.02
0.03
0.12
1.90
2.53
1.66
2.43
168.3
119.0
174.3
115.2
HOH...PyridineN-oxide (54)
-10.69
-10.61
0.08
2.63
2.64
0.01
1.94
1.65
161.0
178.6
MethylethylamineN-oxide...OHH (55)
-15.48
-14.87
0.61
2.49
2.59
0.10
1.83
1.66
148.9
154.6
2.64
2.74
0.11
2.17
2.10
124.2
117.6
Methylethylhydroxylamine...OH2 (56)
-7.41
-7.36
0.05
2.66
2.66
2.79
2.88
0.13
0.22
2.11
2.18
1.94
2.10
138.5
130.2
143.2
135.1
HOH...FCH3 (59)
-4.87
-4.48
0.39
2.70
2.66
-0.04
2.06
1.69
153.9
172.7
HOH...Chloropropane (58)
-3.09
-2.84
0.25
3.34
3.35
0.01
2.82
2.45
143.5
153.9
H2NH...O(CH3)2 (59)
-3.12
-3.43
-0.31
3.00
3.00
0.00
2.32
1.97
155.9
173.9
Methylammonium...OH2 (60)
-19.30
-21.17
-1.87
2.70
2.62
-0.08
1.79
1.57
173.8
176.7
Guanidinium...OHH (61)
-18.48
-19.02
-0.54
2.85
2.85
2.78
2.78
-0.07
-0.07
2.08
2.08
1.87
1.87
147.7
147.7
146.8
146.8
Imidazolium...OH2 (62)
-16.95
-17.60
-0.65
2.71
2.62
-0.08
1.81
1.59
174.5
173.4
Formamidinium...OH2 (63)
-16.98
-18.75
-1.77
2.71
2.61
-0.10
1.91
1.57
148.7
177.2
Formamidinium...OH2, cyclic C2v (64)
-19.59
-19.71
-0.12
2.83
2.78
-0.05
2.09
1.89
142.6
143.6
Formaldehydeiminium...OH2 (65)
-19.98
-21.65
-1.67
2.83
2.66
2.78
2.65
-0.05
-0.01
2.09
1.78
1.89
1.61
142.6
163.4
143.6
176.6
OHH...(-)O2CCH3, bidentate (66)
-21.85
-22.62
-0.77
2.77
2.78
2.74
2.74
-0.03
-0.03
2.06
2.08
1.87
1.87
142.9
141.8
145.7
145.7
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-5.40
1.07
2.73
2.90
0.17
2.03
1.93
172.3
169.6
HOH...HOH, cyclic Cs (2)
-5.02
-4.26
0.76
2.58
2.88
0.30
2.31
2.25
111.8
121.4
2.58
2.88
0.30
2.31
2.25
111.8
121.4
HOH...OHCH3 (3)
-6.10
-4.61
1.49
2.72
2.93
0.22
2.01
1.97
169.0
168.1
CH3OH...OH2 (4)
-6.15
-6.53
-0.38
2.72
2.84
0.11
2.01
1.86
174.9
179.0
CH3OH...OHCH3 (5)
-6.09
-5.65
0.44
2.71
2.86
0.15
2.00
1.89
174.6
179.0
HOH...O(CH3)2 (6)
-5.84
-2.93
2.91
2.71
3.08
0.37
2.02
2.11
163.9
176.3
C6H5OH...OH2 (7)
-8.10
-6.28
1.82
2.67
2.88
0.21
1.95
1.91
174.0
173.8
HOH...OHC6H5 (8)
-5.18
-3.97
1.21
2.79
3.03
0.24
2.12
2.10
160.8
159.3
t-Vinyl alcohol...OH2 (9)
-8.18
-6.32
1.86
2.65
2.85
0.19
1.93
1.87
175.0
179.3
HOH...t-Vinyl alcohol (10)
-5.16
-5.37
-0.21
2.79
2.90
0.12
2.11
1.96
163.2
162.1
HOH...Furan (11)
-4.00
-3.86
0.14
2.78
3.14
0.36
2.22
2.22
141.6
156.6
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-10.57
6.53
2.57
2.57
2.88
2.88
0.31
0.31
1.83
1.83
1.91
1.91
175.9
175.9
169.0
169.0
H3CCOOH...OHH (13)
-10.94
-9.00
1.94
2.58
2.61
2.80
3.03
0.22
0.42
1.90
2.15
1.83
2.48
156.3
127.9
168.3
115.5
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-8.97
2.26
2.54
2.61
2.80
2.88
0.26
0.27
1.80
2.22
1.84
2.29
171.5
122.2
167.3
118.3
-4.90
-4.20
0.70
2.97
2.96
3.16
3.03
0.19
0.07
2.44
2.35
2.21
2.78
141.1
151.7
163.8
95.3
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-3.82
0.00
2.90
3.21
3.05
3.22
0.15
0.01
2.27
2.95
2.27
2.42
155.0
117.5
136.5
139.4
HOH...skew-Methyl vinyl ether (17)
-5.20
-3.78
1.42
2.73
3.03
0.30
2.08
2.09
155.6
160.8
HOH...Methyl formate (=O) (18)
-6.39
-4.58
1.81
2.76
2.98
0.22
2.06
2.00
167.0
179.2
HOH...Methyl formate (-O-) (19)
-3.82
-4.58
-0.76
2.78
4.30
1.52
2.24
3.49
138.7
141.3
HOH...Formaldehyde (20)
-5.81
-3.85
1.96
2.72
2.98
0.27
2.11
2.03
147.6
166.8
HOH...Acetone (21)
-6.87
-4.13
2.74
2.74
2.99
0.25
2.06
2.01
163.1
179.9
t-NMA...OH2 (22)
-5.97
-7.41
-1.44
2.87
2.91
0.04
2.12
1.89
178.3
179.1
HOH...t-NMA (23)
-8.03
-5.67
2.36
2.70
2.95
0.25
2.00
1.98
167.6
172.2
-14.78
-10.02
4.76
2.76
2.76
2.99
2.99
0.23
0.23
2.00
2.00
1.97
1.97
171.6
171.5
177.5
177.5
Formamide dimer, parallel (25)
-8.12
-6.49
1.63
2.80
2.98
0.19
2.09
2.06
156.7
149.8
t-NMA dimer, antiparallel (26)
-7.70
-7.88
-0.18
2.83
2.95
0.12
2.08
1.95
171.8
167.4
t-NMA antiparallel stacked (27)
-3.86
-5.28
-1.42
3.65
3.67
3.84
3.84
0.19
0.17
3.88
3.88
3.69
3.69
87.9
88.9
91.1
91.1
HOH...N-Methylformamide (28)
-7.90
-5.66
2.23
2.71
2.95
0.24
2.01
1.98
164.7
172.1
N-Methylformamide...OH2 (29)
-6.05
-7.43
-1.38
2.84
2.90
0.06
2.09
1.88
173.8
177.0
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-7.50
0.71
2.62
2.82
0.20
1.94
1.88
159.2
160.3
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-8.29
-4.19
2.82
2.82
0.01
2.12
3.49
168.7
40.3
H2NH...HNH2, cyclic C2h (32)
-3.51
-1.29
2.22
3.01
3.01
3.16
3.16
0.15
0.15
2.60
2.61
2.42
2.42
123.9
123.8
130.0
130.0
H2NH...NH3, linear Cs (33)
-3.38
-1.38
2.00
3.15
3.15
3.20
3.20
0.05
0.05
2.42
3.64
2.19
3.25
179.0
69.8
177.7
78.4
HOH...NH3 (34)
-7.22
-3.75
3.47
2.80
2.97
0.18
2.09
2.00
176.4
173.6
HOH...NH2CH3 (35)
-7.07
-3.58
3.50
2.80
3.04
0.24
2.09
2.08
175.9
169.3
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-7.81
-0.81
2.79
2.85
0.06
2.03
1.82
178.2
178.0
HOH...Imidazole (37)
-7.77
-6.05
1.72
2.73
3.14
0.41
2.10
2.25
151.2
150.0
Indole...OH2 (38)
-6.33
-6.82
-0.49
2.81
2.88
0.07
2.07
1.84
168.3
175.7
Pyrrole...OH2 (39)
-5.89
-6.28
-0.39
2.82
2.89
0.07
2.07
1.85
180.0
180.0
HOH...Pyridine (40)
-6.63
-4.25
2.38
2.77
3.20
0.42
2.12
2.32
155.8
148.8
Formamidine...H2O, cyclic (41)
-11.03
-8.51
2.52
2.81
2.70
2.98
2.90
0.17
0.20
2.20
2.06
2.11
1.92
143.3
151.4
142.5
171.2
HOH...Formaldehydeimine (42)
-6.74
-5.91
0.83
2.76
2.90
0.14
2.11
1.92
154.0
179.6
Guanidine...OHH (43)
-7.96
-7.00
0.96
2.88
2.77
3.01
2.97
0.13
0.20
2.25
2.21
2.10
2.06
145.4
141.1
148.2
152.8
Vinylamine...OH2 (44)
-3.80
-4.33
-0.53
3.04
2.98
-0.06
2.19
1.97
164.2
177.0
Aniline...OH2 (45)
-4.62
-5.17
-0.55
2.94
2.93
-0.01
2.20
1.91
173.2
175.0
HSH...OH2 (46)
-2.93
-2.19
0.74
3.33
3.58
0.25
2.29
2.84
175.3
113.4
HOH...S(CH3)2 (47)
-3.56
-2.05
1.51
3.12
3.12
3.28
3.28
0.16
0.16
3.13
3.13
2.30
3.64
97.7
97.7
178.2
60.6
OHH...CH3SSCH3, cyclic (48)
-3.78
-1.71
2.07
3.38
3.47
0.09
2.84
2.50
147.0
172.9
HOH...Thiophene (49)
-2.66
-4.36
-1.70
3.59
3.59
3.63
3.63
0.04
0.04
3.50
3.33
3.57
2.91
108.4
121.0
85.7
131.4
HOH...SHC6H5 (50)
-2.20
-4.38
-2.18
4.56
4.40
-0.16
4.27
3.77
132.4
125.0
HSH...SH2 (51)
-0.96
-1.23
-0.26
4.15
3.77
-0.38
3.19
3.02
175.5
114.4
HOH...SH2 (52)
-2.27
-2.75
-0.48
3.47
3.09
-0.38
2.83
2.13
175.5
167.5
CH3COOH...NH3, bidentate (53)
-11.94
-6.04
5.90
2.63
2.89
2.86
3.27
0.23
0.37
1.90
2.53
1.88
2.74
168.3
119.0
177.6
112.8
HOH...PyridineN-oxide (54)
-10.69
-7.20
3.49
2.63
2.87
0.24
1.94
1.89
161.0
177.3
MethylethylamineN-oxide...OHH( 55)
-15.48
-21.09
-5.60
2.49
3.45
0.96
1.83
3.83
148.9
59.9
2.64
2.73
0.09
2.17
1.72
124.2
170.5
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.51
0.90
2.66
2.66
2.84
3.58
0.18
0.92
2.11
2.18
1.87
3.99
138.5
130.2
173.0
58.3
HOH...FCH3 (59)
-4.87
-1.69
3.17
2.70
3.09
0.39
2.06
2.13
153.9
169.7
HOH...Chloropropane (58)
-3.09
-1.09
1.99
3.34
4.43
1.10
2.82
3.81
143.5
125.0
H2NH...O(CH3)2 (59)
-3.12
-1.18
1.94
3.00
3.36
0.36
2.32
2.35
155.9
179.8
Methylammonium...OH2 (60)
-19.30
-18.81
0.49
2.70
2.74
0.04
1.79
1.74
173.8
167.9
Guanidinium...OHH (61)
-18.48
-16.40
2.08
2.85
2.85
2.96
2.96
0.11
0.11
2.08
2.08
2.02
2.02
147.7
147.7
152.4
152.4
Imidazolium...OH2 (62)
-16.95
-15.95
1.00
2.71
2.78
0.07
1.81
1.74
174.5
172.4
OHH...(-)O2CCH3, bidentate (66)
-21.85
-17.22
4.63
2.77
2.78
2.86
2.86
0.09
0.08
2.06
2.08
2.00
2.00
142.9
141.8
143.9
143.9
a
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.40
0.07
2.73
2.76
0.03
2.03
1.79
172.3
173.7
HOH...HOH, cyclic Cs (2)
-5.02
-4.74
0.28
2.58
2.81
0.23
2.31
2.17
111.8
122.3
2.58
2.81
0.23
2.31
2.17
111.8
122.3
HOH...OHCH3 (3)
-6.10
-4.41
1.69
2.72
2.81
0.09
2.01
1.85
169.0
168.0
CH3OH...OH2 (4)
-6.15
-6.78
-0.63
2.72
2.66
-0.06
2.01
1.68
174.9
176.0
CH3OH...OHCH3 (5)
-6.09
-5.03
1.06
2.71
2.69
-0.02
2.00
1.72
174.6
174.9
HOH...O(CH3)2 (6)
-5.84
-5.09
0.75
2.71
2.79
0.08
2.02
1.82
163.9
173.5
C6H5OH...OH2 (7)
-8.10
-7.57
0.53
2.67
2.67
0.01
1.95
1.71
174.0
169.3
HOH...OHC6H5 (8)
-5.18
-4.18
1.00
2.79
2.83
0.05
2.12
1.88
160.8
167.9
t-Vinyl alcohol...OH2 (9)
-8.18
-7.33
0.85
2.65
2.66
0.00
1.93
1.68
175.0
177.2
HOH...t-Vinyl alcohol (10)
-5.16
-4.31
0.85
2.79
2.81
0.02
2.11
1.85
163.2
167.5
HOH...Furan (11)
-4.00
-3.87
0.13
2.78
2.93
0.15
2.22
2.01
141.6
158.4
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-11.14
5.96
2.57
2.57
2.66
2.66
0.09
0.09
1.83
1.83
1.70
1.70
175.9
175.9
171.7
171.7
H3CCOOH...OHH (13)
-10.94
-8.82
2.12
2.58
2.61
2.66
3.00
0.08
0.39
1.90
2.15
1.70
2.40
156.3
127.9
168.5
119.5
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.31
1.92
2.54
2.61
2.65
2.74
0.11
0.13
1.80
2.22
1.68
2.05
171.5
122.2
170.4
126.9
-4.90
-4.24
0.66
2.97
2.96
3.52
2.80
0.55
-0.15
2.44
2.35
3.02
1.83
141.1
151.7
113.9
177.7
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.31
-5.49
2.90
3.21
2.74
4.83
-0.16
1.62
2.27
2.95
2.05
5.72
155.0
117.5
126.9
21.0
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.85
0.36
2.73
2.79
0.06
2.08
1.84
155.6
165.6
HOH...Methyl formate (=O) (18)
-6.39
-6.19
0.20
2.76
2.75
-0.01
2.06
1.77
167.0
176.7
HOH...Methyl formate (-O-) (19)
-3.82
-3.20
0.62
2.78
4.04
1.27
2.24
4.34
138.7
65.9
HOH...Formaldehyde (20)
-5.81
-6.01
-0.20
2.72
2.75
0.03
2.11
1.78
147.6
174.5
HOH...Acetone (21)
-6.87
-5.30
1.57
2.74
2.76
0.02
2.06
1.79
163.1
179.2
t-NMA...OH2 (22)
-5.97
-4.19
1.78
2.87
3.07
0.20
2.12
2.04
178.3
176.8
HOH...t-NMA (23)
-8.03
-6.80
1.23
2.70
2.74
0.04
2.00
1.77
167.6
175.6
-14.78
-6.53
8.25
2.76
2.76
3.00
3.00
0.24
0.24
2.00
2.00
1.97
1.97
171.6
171.5
175.9
175.9
Formamide dimer, parallel (25)
-8.12
-5.23
2.89
2.80
3.08
0.29
2.09
2.28
156.7
133.4
t-NMA dimer, antiparallel (26)
-7.70
-5.69
2.01
2.83
3.02
0.19
2.08
2.00
171.8
168.8
t-NMA antiparallel stacked (27)
-3.86
-4.84
-0.98
3.65
3.67
4.00
4.00
0.35
0.33
3.88
3.88
3.82
3.82
87.9
88.9
92.7
92.7
HOH...N-Methylformamide (28)
-7.90
-7.18
0.72
2.71
2.73
0.02
2.01
1.76
164.7
172.1
N-Methylformamide...OH2 (29)
-6.05
-4.46
1.59
2.84
3.05
0.21
2.09
2.02
173.8
169.3
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.40
-0.19
2.62
2.64
0.02
1.94
1.68
159.2
168.0
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-9.06
-4.97
2.82
2.65
-0.17
2.12
3.31
168.7
40.6
H2NH...HNH2, cyclic C2h (32)
-3.51
-0.46
3.05
3.01
3.01
3.69
3.69
0.69
0.69
2.60
2.61
2.92
2.92
123.9
123.8
132.8
132.8
H2NH...NH3, linear Cs (33)
-3.38
-0.50
2.88
3.15
3.15
3.69
3.69
0.53
0.53
2.42
3.64
2.66
3.80
179.0
69.8
176.0
76.0
HOH...NH3 (34)
-7.22
-1.99
5.23
2.80
3.18
0.39
2.09
2.22
176.4
173.1
HOH...NH2CH3 (35)
-7.07
-4.05
3.02
2.80
3.07
0.27
2.09
2.10
175.9
178.7
Formamide dimer, cyclic (24)
Indole...OH2 (38)
-6.33
-2.59
3.74
2.81
3.09
0.28
2.07
2.06
168.3
176.9
Pyrrole...OH2 (39)
-5.89
-2.28
3.61
2.82
3.11
0.29
2.07
2.07
180.0
180.0
HOH...Pyridine (40)
-6.63
-3.36
3.27
2.77
3.48
0.70
2.12
3.26
155.8
95.0
Formamidine...H2O, cyclic (41)
-11.03
-3.49
7.54
2.81
2.70
3.21
3.18
0.40
0.48
2.20
2.06
2.28
2.25
143.3
151.4
150.4
160.8
HOH...Formaldehydeimine (42)
-6.74
-3.00
3.74
2.76
3.17
0.41
2.11
2.23
154.0
162.4
Guanidine...OHH (43)
-7.96
-5.74
2.22
2.88
2.77
3.16
3.16
0.28
0.40
2.25
2.21
2.19
3.80
145.4
141.1
157.1
42.7
Vinylamine...OH2 (44)
-3.80
-1.76
2.03
3.04
3.15
0.11
2.19
2.12
164.2
179.7
Aniline...OH2 (45)
-4.62
-2.82
1.80
2.94
3.12
0.18
2.20
2.09
173.2
179.9
HSH...OH2 (46)
-2.93
-0.98
1.95
3.33
3.48
0.15
2.29
2.94
175.3
102.6
HOH...S(CH3)2 (47)
-3.56
-1.23
2.33
3.12
3.12
3.40
3.40
0.29
0.29
3.13
3.13
3.60
2.46
97.7
97.7
70.4
166.0
OHH...CH3SSCH3, cyclic (48)
-3.78
-1.32
2.46
3.38
3.41
0.03
2.84
2.48
147.0
162.6
HOH...Thiophene (49)
-2.66
-3.76
-1.10
3.59
3.59
3.49
3.49
-0.10
-0.10
3.50
3.33
3.75
2.79
108.4
121.0
66.7
129.3
HOH...SHC6H5 (50)
-2.20
-3.45
-1.25
4.56
4.56
-0.01
4.27
3.99
132.4
120.4
HSH...SH2 (51)
-0.96
-0.46
0.50
4.15
3.51
-0.64
3.19
3.13
175.5
94.8
HOH...SH2 (52)
-2.27
-1.54
0.73
3.47
3.04
-0.43
2.83
2.09
175.5
171.7
CH3COOH...NH3, bidentate (53)
-11.94
-2.95
8.99
2.63
2.89
3.05
3.43
0.42
0.53
1.90
2.53
2.09
2.84
168.3
119.0
176.2
116.9
HOH...PyridineN-oxide (54)
-10.69
-3.53
7.16
2.63
3.82
1.19
1.94
4.26
161.0
57.4
MethylethylamineN-oxide...OHH( 55)
-15.48
-16.58
-1.10
2.49
2.64
3.50
2.84
1.01
0.21
1.83
2.17
3.85
1.80
148.9
124.2
62.2
174.1
Methylethylhydroxylamine...OH2 (56)
-7.41
-6.99
0.43
2.66
2.80
0.15
2.11
2.03
138.5
135.8
2.66
2.97
0.31
2.18
2.08
130.2
151.5
HOH...FCH3 (59)
-4.87
-3.91
0.96
2.70
2.81
0.10
2.06
1.84
153.9
175.5
HOH...Chloropropane (58)
-3.09
-3.16
-0.08
3.34
3.09
-0.25
2.82
2.12
143.5
178.1
H2NH...O(CH3)2 (59)
-3.12
-1.44
1.68
3.00
3.29
0.29
2.32
2.27
155.9
177.7
Methylammonium...OH2 (60)
-19.30
-17.49
1.81
2.70
2.81
0.11
1.79
1.76
173.8
177.2
Guanidinium...OHH (61)
-18.48
-5.50
12.98
2.85
2.85
3.20
3.53
0.34
0.68
2.08
2.08
3.48
3.76
147.7
147.7
65.9
69.1
Imidazolium...OH2 (62)
-16.95
-13.21
3.74
2.71
2.86
0.16
1.81
1.82
174.5
175.5
Formamidinium...OH2 (63)
-16.98
-2.40
14.58
2.71
3.11
0.41
1.91
2.08
148.7
179.3
Formamidinium...OH2, cyclic C2v (64)
-19.59
-3.20
16.39
2.83
3.24
0.40
2.09
2.24
142.6
162.5
2.83
3.24
0.40
2.09
2.24
142.6
162.5
2.77
2.78
2.69
2.69
-0.07
-0.08
2.06
2.08
1.81
1.81
142.9
141.8
147.2
147.2
OHH...(-)O2CCH3, bidentate (66)
a
-21.85
-22.84
-0.99
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
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
HOH...OH2 (1)
-6.47
-6.83
-0.36
2.73
2.76
0.02
2.03
1.78
172.3
173.3
HOH...HOH, cyclic Cs (2)
-5.02
-6.75
-1.73
2.58
2.76
0.18
2.31
1.78
111.8
177.5
2.58
2.76
0.18
2.31
3.21
111.8
53.9
HOH...OHCH3 (3)
-6.10
-6.24
-0.14
2.72
2.87
0.16
2.01
1.99
169.0
151.9
CH3OH...OH2 (4)
-6.15
-5.19
0.96
2.72
2.97
0.25
2.01
2.02
174.9
171.7
CH3OH...OHCH3 (5)
-6.09
-6.49
-0.39
2.71
2.77
0.06
2.00
1.84
174.6
163.0
HOH...O(CH3)2 (6)
-5.84
-4.59
1.25
2.71
2.93
0.22
2.02
2.10
163.9
142.7
C6H5OH...OH2 (7)
-8.10
-5.66
2.44
2.67
2.98
0.31
1.95
2.03
174.0
179.5
HOH...OHC6H5 (8)
-5.18
-6.75
-1.57
2.79
2.87
0.08
2.12
2.00
160.8
150.2
t-Vinyl alcohol...OH2 (9)
-8.18
-6.25
1.93
2.65
2.95
0.29
1.93
1.99
175.0
179.1
HOH...t-Vinyl alcohol (10)
-5.16
-5.06
0.10
2.79
2.87
0.08
2.11
2.15
163.2
130.4
HOH...Furan (11)
-4.00
-3.36
0.64
2.78
3.25
0.46
2.22
2.78
141.6
110.9
H3CCOOH...HOOCCH3, cyclic (12)
-17.10
-3.56
13.54
2.57
2.57
2.89
2.89
0.32
0.32
1.83
1.83
1.94
1.94
175.9
175.9
170.4
170.4
H3CCOOH...OHH (13)
-10.94
-6.30
4.64
2.58
2.61
3.22
2.82
0.64
0.21
1.90
2.15
2.40
1.99
156.3
127.9
144.0
143.4
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-4.15
7.08
2.54
2.61
3.16
2.74
0.62
0.12
1.80
2.22
2.21
1.96
171.5
122.2
174.9
135.6
-4.90
-7.25
-2.35
2.97
2.96
2.94
2.80
-0.03
-0.15
2.44
2.35
2.05
2.70
141.1
151.7
154.5
85.9
OHH...cis,cis-Oxalic acid, cyclic (15)
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-6.61
-2.79
2.90
3.21
2.84
2.91
-0.06
-0.30
2.27
2.95
2.07
2.09
155.0
117.5
136.2
141.9
HOH...skew-Methyl vinyl ether (17)
-5.20
-4.79
0.41
2.73
2.90
0.17
2.08
2.13
155.6
135.7
HOH...Methyl formate (=O) (18)
-6.39
-7.47
-1.08
2.76
2.90
0.14
2.06
1.97
167.0
162.0
HOH...Methyl formate (-O-) (19)
-3.82
-5.68
-1.86
2.78
2.96
0.19
2.24
2.06
138.7
154.8
HOH...Formaldehyde (20)
-5.81
-5.59
0.22
2.72
2.88
0.16
2.11
2.02
147.6
148.0
HOH...Acetone (21)
-6.87
-6.18
0.70
2.74
2.91
0.17
2.06
1.98
163.1
161.1
t-NMA...OH2 (22)
-5.97
-5.20
0.77
2.87
3.11
0.25
2.12
2.11
178.3
179.3
HOH...t-NMA (23)
-8.03
-6.87
1.16
2.70
2.90
0.20
2.00
1.99
167.6
158.0
-14.78
-11.68
3.11
2.76
2.76
2.91
2.91
0.15
0.15
2.00
2.00
1.90
1.90
171.6
171.5
176.2
176.2
Formamide dimer, parallel (25)
-8.12
-8.38
-0.26
2.80
2.85
0.05
2.09
1.95
156.7
147.1
t-NMA dimer, antiparallel (26)
-7.70
-7.83
-0.13
2.83
2.82
-0.01
2.08
1.97
171.8
140.6
t-NMA antiparallel stacked (27)
-3.86
-8.08
-4.22
3.65
3.67
3.39
3.39
-0.26
-0.28
3.88
3.88
3.55
3.55
87.9
88.9
72.8
72.8
HOH...N-Methylformamide (28)
-7.90
-6.81
1.09
2.71
2.96
0.26
2.01
2.01
164.7
173.0
N-Methylformamide...OH2 (29)
-6.05
-5.39
0.66
2.84
3.08
0.24
2.09
2.08
173.8
177.0
t-N-OH,N-Meacetamide...OH2 (30)
-8.21
-8.21
0.00
2.62
2.90
0.28
1.94
2.08
159.2
143.6
HOH...t-N-OH,N-Methylacetamide (31)
-4.10
-8.21
-4.11
2.82
2.90
0.09
2.12
3.46
168.7
48.2
H2NH...HNH2, cyclic C2h (32)
-3.51
-5.60
-2.09
3.01
3.01
2.75
2.75
-0.26
-0.26
2.60
2.61
2.03
2.03
123.9
123.8
125.8
125.8
H2NH...NH3, linear Cs (33)
-3.38
-4.52
-1.14
3.15
3.15
2.75
2.75
-0.40
-0.40
2.42
3.64
2.03
2.03
179.0
69.8
125.8
125.8
HOH...NH3 (34)
-7.22
-6.39
0.82
2.80
2.96
0.16
2.09
2.02
176.4
162.9
HOH...NH2CH3 (35)
-7.07
-2.43
4.65
2.80
3.15
0.36
2.09
2.26
175.9
155.6
Formamide dimer, cyclic (24)
Imidazole...OH2 (36)
-7.00
-10.83
-3.83
2.79
2.94
0.15
2.03
1.96
178.2
176.0
HOH...Imidazole (37)
-7.77
-7.42
0.35
2.73
2.81
0.08
2.10
2.32
151.2
111.4
Indole...OH2 (38)
-6.33
-5.31
1.01
2.81
3.04
0.24
2