Directory UMM :wiley:Public:journals:jcc:suppmat:20:
Table B-I. _____________________________________________________________________________
Consensus BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.72
0.74
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.3
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
-6.11
-5.42
0.69
2.58
2.72
2.82
2.79
0.24
0.07
2.31
2.01
2.24
1.83
111.8
171.0
117.3
166.8
-6.15
-5.49
0.66
2.72
2.77
0.05
2.01
1.79
174.9
178.1
-6.09
-5.31
0.78
2.71
2.77
0.06
2.00
1.79
174.5
178.3
-5.84
-4.85
0.99
2.71
2.84
0.13
2.02
1.89
163.8
165.1
-8.10
-7.06
1.04
2.67
2.74
0.07
1.95
1.77
174.0
167.3
-5.18
-4.22
0.96
2.79
2.88
0.09
2.12
1.95
160.8
159.1
-8.18
-7.24
0.93
2.65
2.72
0.07
1.93
1.74
175.0
176.1
-5.16
-4.00
-17.10
-4.39
-3.02
-13.14
0.77
0.99
3.96
2.79
2.78
2.57
2.88
3.29
2.69
0.09
0.50
0.12
2.11
2.22
1.83
1.94
2.53
1.71
163.2
141.6
175.9
159.1
134.6
167.8
H3CCOOH...OHH (13)
-11.72
-9.20
2.53
2.57
2.59
2.69
2.72
0.12
0.14
1.83
1.90
1.71
1.77
175.9
158.1
167.8
161.6
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.72
1.51
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-5.07
-0.17
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.72b
-5.90
2.59
2.54
2.61
2.97
2.96
2.90
2.72
2.69
2.65
3.01
2.81
2.65
0.14
0.15
0.03
0.04
-0.14
-0.26
3.42
1.80
2.22
2.44
2.35
2.27
3.69
1.70
1.97
2.11
2.72
1.97
43.9
171.5
122.3
141.0
151.9
155.0
7.1
173.7
124.3
153.4
85.4
124.3
1.40
0.47
1.92
0.40
3.21
2.73
2.76
2.78
2.72
4.74
2.96
2.77
2.99
2.76
1.53
0.22
0.01
0.21
0.05
2.95
2.08
2.06
2.24
2.11
5.63
2.04
1.79
2.12
1.79
117.5
155.6
167.0
138.7
147.6
20.9
155.4
177.0
148.4
169.9
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
-3.80
-5.92
-1.90
-5.41
Bush, Bayly, Halgren 4/5/99 SM B - 1 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.06
-6.28
0.81
-0.31
2.74
2.87
2.75
2.86
0.01
0.00
2.06
2.12
1.78
1.84
163.2
178.4
175.2
178.1
-8.03
-14.78
-7.01
-10.69
1.01
4.09
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-6.49
-8.24
-5.58
1.64
-0.54
-0.23
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-6.72
-6.47
1.18
-0.42
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.75
2.84
2.84
2.80
2.80
3.61
3.61
2.76
2.84
0.05
0.08
0.08
0.00
-0.03
0.03
0.03
0.05
0.00
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.77
1.83
1.83
1.78
1.79
3.48
3.48
1.78
1.82
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
172.8
170.9
170.9
175.4
166.4
88.9
88.9
174.2
174.6
-8.21
-7.28
0.93
2.62
2.73
0.11
1.94
1.75
159.3
176.0
-4.10
-3.51
-3.68
-2.98
0.42
0.53
2.82
3.01
2.87
3.11
0.06
0.10
2.12
2.61
1.90
2.40
168.5
123.7
178.0
125.4
-0.23
3.01
3.15
3.11
3.04
0.10
-0.12
2.60
2.42
2.40
2.01
124.0
179.0
125.4
178.1
3.04
2.82
-0.12
0.03
3.64
2.09
3.37
1.84
69.8
176.4
62.7
173.8
H2NH...NH3, linear Cs (33)
-3.38
-3.61
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.28
0.94
3.15
2.80
-7.18
-5.80
1.38
2.77
2.88
0.11
2.06
1.90
170.6
172.7
-7.00
-6.48
0.52
2.79
2.87
0.08
2.03
1.85
177.9
177.1
-7.77
-6.33
-5.86
-5.92
1.91
0.41
2.73
2.81
2.83
2.88
0.09
0.07
2.10
2.07
1.90
1.86
151.1
168.3
156.6
179.0
-5.89
-5.36
0.54
2.82
2.89
0.07
2.07
1.87
179.5
180.0
-6.63
-11.03
-4.99
-8.55
1.64
2.48
2.77
2.82
2.88
3.05
0.11
0.23
2.12
2.20
1.96
2.18
155.6
143.2
157.7
142.2
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-6.50
-6.12
0.24
1.84
Vinylamine...OH2 (44)
-3.80
-4.34
-0.54
2.70
2.76
2.88
2.77
3.04
2.81
2.78
2.98
2.97
2.90
0.11
0.03
0.10
0.20
-0.14
2.05
2.11
2.25
2.20
2.20
1.86
1.81
2.06
2.14
1.87
151.5
153.9
145.4
141.1
163.8
161.4
168.5
147.8
141.6
174.3
Bush, Bayly, Halgren 4/5/99 SM B - 2 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.46
0.17
2.94
2.91
-0.03
2.20
1.88
173.4
172.7
-2.93
-2.61
0.32
3.33
3.41
0.08
2.29
2.07
175.3
172.6
-3.56
-2.81
0.75
3.12
3.45
0.33
3.13
2.48
97.9
172.2
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.50
1.28
3.12
3.38
3.45
3.63
0.33
0.26
3.13
2.84
3.87
2.67
97.6
147.0
57.5
174.5
-2.66
-2.83
-0.17
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.83
-0.63
3.59
3.59
4.56
3.74
3.74
4.33
0.15
0.15
-0.23
3.50
3.33
4.27
2.92
3.59
3.51
108.4
121.0
132.4
142.2
91.1
143.4
-0.96
-1.17
-0.21
4.15
4.04
-0.11
3.19
2.71
175.6
167.2
-2.27
-1.81
0.46
3.47
3.52
0.04
2.83
2.58
175.5
163.0
-11.94
-9.52
2.42
2.63
2.72
0.09
1.90
1.73
168.3
172.3
3.06
2.74
2.69
3.06
2.77
0.17
0.11
0.20
0.42
0.11
2.53
1.94
1.83
2.17
2.10
2.45
1.76
1.74
2.53
1.79
119.0
161.0
148.9
124.2
140.6
117.1
179.2
162.8
110.8
179.1
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-7.75
-9.21
2.94
6.27
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.08
3.05
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.43
1.44
2.69
2.70
3.36
2.74
0.67
0.04
2.19
2.06
3.44
1.77
133.1
153.8
77.2
176.9
-3.09
-2.83
-2.76
-3.02
0.33
-0.20
3.34
3.04
3.36
3.08
0.03
0.05
2.82
2.36
2.42
2.06
143.6
155.9
162.1
174.7
-19.30
-18.43
0.86
2.70
2.68
-0.02
1.79
1.64
173.7
173.5
-18.48
-18.83
-0.35
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.12
-0.17
2.85
2.85
2.71
2.77
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.3
175.9
-16.98
-17.98
-1.01
2.70
2.61
-0.09
1.91
1.58
148.7
176.1
-19.59
-18.95
0.64
2.83
2.79
-0.05
2.09
1.89
142.6
144.5
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-20.19
-0.20
2.83
2.66
2.79
2.64
-0.05
-0.02
2.09
1.77
1.89
1.60
142.6
163.4
144.5
177.6
-21.85
-19.39
2.46
2.77
2.79
0.02
2.06
1.93
142.8
144.5
2.78
2.79
0.01
2.08
1.93
141.8
144.5
Bush, Bayly, Halgren 4/5/99 SM B - 3 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 4 -
Table B-II. _________________________________________________________________________________________________
Single-molecule BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.72
0.74
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.3
-6.11
-5.36
0.75
2.58
2.72
2.82
2.78
0.24
0.06
2.31
2.01
2.24
1.81
111.8
171.0
117.3
168.1
-6.15
-5.58
0.57
2.72
2.77
0.05
2.01
1.79
174.9
179.8
-6.09
-5.37
0.72
2.71
2.76
0.05
2.00
1.78
174.5
177.2
-5.84
-3.98
1.87
2.71
2.90
0.19
2.02
1.95
163.8
165.5
-8.10
-6.33
1.77
2.67
2.77
0.10
1.95
1.80
174.0
167.4
-5.18
-3.87
1.31
2.79
2.91
0.12
2.12
1.98
160.8
157.9
-8.18
-8.12
0.06
2.65
2.69
0.04
1.93
1.70
175.0
176.0
-5.16
-4.00
-17.10
-4.90
-2.93
-15.19
0.26
1.07
1.91
2.79
2.78
2.57
2.84
3.31
2.65
0.05
0.53
0.08
2.11
2.22
1.83
1.90
2.56
1.67
163.2
141.6
175.9
160.7
134.0
168.1
2.57
2.59
2.65
2.74
0.08
0.15
1.83
1.90
1.67
1.79
175.9
158.1
168.1
160.4
2.74
2.71
2.67
3.03
2.82
2.67
0.15
0.17
0.06
0.06
-0.13
-0.23
3.42
1.80
2.22
2.44
2.35
2.27
3.71
1.73
2.00
2.13
2.72
2.00
43.9
171.5
122.3
141.0
151.9
155.0
4.8
172.8
123.5
153.4
86.1
123.5
4.77
2.93
2.74
2.94
2.81
1.56
0.20
-0.01
0.17
0.09
2.95
2.08
2.06
2.24
2.11
5.67
2.01
1.76
1.97
1.84
117.5
155.6
167.0
138.7
147.6
20.4
157.9
175.0
173.2
169.9
H3CCOOH...OHH (13)
-11.72
-9.54
2.18
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.02
2.20
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.73
0.17
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.02b
-5.21
2.59
2.54
2.61
2.97
2.96
2.90
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
-4.02
-6.65
-2.56
-4.61
1.18
-0.26
1.26
1.20
3.21
2.73
2.76
2.78
2.72
Bush, Bayly, Halgren 4/5/99 SM B - 5 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-5.94
-5.61
0.93
0.36
2.74
2.87
2.75
2.90
0.01
0.04
2.06
2.12
1.77
1.88
163.2
178.4
176.0
178.5
-8.03
-14.78
-7.37
-13.04
0.65
1.74
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-8.26
-7.77
-5.98
-0.14
-0.07
-0.63
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-6.88
-5.45
1.02
0.60
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.72
2.78
2.78
2.77
2.80
3.52
3.52
2.75
2.90
0.02
0.02
0.02
-0.03
-0.03
-0.06
-0.06
0.04
0.06
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.75
1.76
1.76
1.80
1.79
3.47
3.47
1.77
1.88
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
173.6
171.7
171.7
155.9
167.1
84.8
84.8
175.7
173.8
-8.21
-7.22
0.99
2.62
2.73
0.11
1.94
1.75
159.3
175.6
-4.10
-3.51
-3.85
-4.02
0.25
-0.51
2.82
3.01
2.87
3.08
0.05
0.07
2.12
2.61
1.90
2.37
168.5
123.7
175.0
125.1
-0.64
3.01
3.15
3.08
3.01
0.07
-0.15
2.60
2.42
2.37
1.97
124.0
179.0
125.1
178.2
3.01
2.81
-0.15
0.01
3.64
2.09
3.34
1.83
69.8
176.4
62.4
173.9
H2NH...NH3, linear Cs (33)
-3.38
-4.02
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.63
0.59
3.15
2.80
-7.18
-5.61
1.57
2.77
2.87
0.10
2.06
1.90
170.6
173.0
-7.00
-6.42
0.58
2.79
2.87
0.08
2.03
1.85
177.9
176.5
-7.77
-6.33
-6.15
-6.15
1.62
0.18
2.73
2.81
2.81
2.86
0.07
0.06
2.10
2.07
1.87
1.84
151.1
168.3
158.6
179.1
-5.89
-5.69
0.20
2.82
2.88
0.06
2.07
1.86
179.5
180.0
-6.63
-11.03
-5.03
-8.59
1.60
2.44
2.77
2.82
2.88
3.02
0.11
0.20
2.12
2.20
1.95
2.14
155.6
143.2
158.5
143.6
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.58
-7.26
1.16
0.69
Vinylamine...OH2 (44)
-3.80
-4.14
-0.34
2.70
2.76
2.88
2.77
3.04
2.81
2.84
2.96
2.86
2.91
0.12
0.08
0.08
0.10
-0.13
2.05
2.11
2.25
2.20
2.20
1.87
1.87
2.04
2.01
1.89
151.5
153.9
145.4
141.1
163.8
160.1
166.7
149.5
144.6
174.3
Bush, Bayly, Halgren 4/5/99 SM B - 6 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.40
0.22
2.94
2.91
-0.03
2.20
1.89
173.4
172.6
-2.93
-2.67
0.26
3.33
3.40
0.07
2.29
2.06
175.3
172.7
-3.56
-3.06
0.50
3.12
3.47
0.35
3.13
2.50
97.9
173.7
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.67
1.12
3.12
3.38
3.47
3.63
0.35
0.25
3.13
2.84
3.88
2.66
97.6
147.0
58.6
172.7
-2.66
-2.95
-0.29
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.84
-0.65
3.59
3.59
4.56
3.72
3.72
4.34
0.13
0.13
-0.22
3.50
3.33
4.27
2.84
3.69
3.53
108.4
121.0
132.4
151.0
84.4
143.3
-0.96
-1.21
-0.24
4.15
4.03
-0.12
3.19
2.71
175.6
167.2
-2.27
-1.84
0.42
3.47
3.51
0.04
2.83
2.57
175.5
163.1
-11.94
-10.18
1.76
2.63
2.71
0.08
1.90
1.72
168.3
170.5
2.97
2.71
2.69
3.06
2.75
0.08
0.08
0.20
0.42
0.09
2.53
1.94
1.83
2.17
2.10
2.31
1.73
1.74
2.53
1.77
119.0
161.0
148.9
124.2
140.6
120.9
177.4
162.8
110.8
178.5
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-8.34
-9.22
2.35
6.26
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.47
2.65
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.49
1.38
2.69
2.70
3.37
2.73
0.68
0.03
2.19
2.06
3.53
1.76
133.1
153.8
72.8
175.5
-3.09
-2.83
-2.72
-2.65
0.37
0.18
3.34
3.04
3.36
3.14
0.03
0.10
2.82
2.36
2.44
2.11
143.6
155.9
158.7
175.4
-19.30
-18.33
0.97
2.70
2.68
-0.02
1.79
1.64
173.7
170.8
-18.48
-18.83
-0.35
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.12
-0.17
2.85
2.85
2.71
2.77
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.3
175.9
-16.98
-17.98
-1.01
2.70
2.61
-0.09
1.91
1.58
148.7
176.1
-19.59
-18.95
0.64
2.83
2.79
-0.05
2.09
1.89
142.6
144.5
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-18.16
1.83
2.83
2.66
2.79
2.70
-0.05
0.04
2.09
1.77
1.89
1.66
142.6
163.4
144.5
179.2
-21.85
-19.49
2.35
2.77
2.79
0.02
2.06
1.92
142.8
144.6
2.78
2.79
0.01
2.08
1.92
141.8
144.6
Bush, Bayly, Halgren 4/5/99 SM B - 7 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 8 -
Table B-III. _________________________________________________________________________________________________
Unique-bond BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.71
0.76
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.1
-6.11
-5.85
0.26
2.58
2.72
2.82
2.75
0.24
0.04
2.31
2.01
2.23
1.79
111.8
171.0
117.5
167.9
-6.15
-6.37
-0.22
2.72
2.73
0.01
2.01
1.75
174.9
179.1
-6.09
-6.62
-0.53
2.71
2.69
-0.02
2.00
1.71
174.5
177.6
-5.84
-4.27
1.58
2.71
2.87
0.16
2.02
1.92
163.8
164.7
-8.10
-7.38
0.72
2.67
2.72
0.06
1.95
1.76
174.0
166.3
-5.18
-5.01
0.18
2.79
2.80
0.01
2.12
1.84
160.8
164.2
-8.18
-7.68
0.50
2.65
2.72
0.06
1.93
1.73
175.0
178.1
-5.16
-4.00
-17.10
-5.08
-2.93
-15.14
0.08
1.07
1.97
2.79
2.78
2.57
2.82
3.31
2.65
0.03
0.52
0.08
2.11
2.22
1.83
1.88
2.56
1.67
163.2
141.6
175.9
160.9
134.3
168.1
2.57
2.59
2.65
2.74
0.08
0.15
1.83
1.90
1.67
1.78
175.9
158.1
168.1
160.7
2.74
2.71
2.67
3.03
2.83
2.67
0.15
0.17
0.06
0.06
-0.13
-0.23
3.42
1.80
2.22
2.44
2.35
2.27
3.70
1.73
2.00
2.13
2.72
2.00
43.9
171.5
122.3
141.0
151.9
155.0
5.1
172.7
123.5
153.6
86.3
123.6
4.77
2.92
2.74
2.94
2.81
1.55
0.18
-0.01
0.17
0.09
2.95
2.08
2.06
2.24
2.11
5.67
1.99
1.76
1.97
1.84
117.5
155.6
167.0
138.7
147.6
20.4
157.9
175.0
173.2
170.0
H3CCOOH...OHH (13)
-11.72
-9.57
2.15
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.01
2.22
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.72
0.18
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.01b
-5.21
2.59
2.54
2.61
2.97
2.96
2.90
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
-4.04
-6.67
-2.56
-4.62
1.16
-0.28
1.26
1.19
3.21
2.73
2.76
2.78
2.72
Bush, Bayly, Halgren 4/5/99 SM B - 9 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.06
-5.90
0.81
0.07
2.74
2.87
2.75
2.88
0.00
0.01
2.06
2.12
1.77
1.86
163.2
178.4
176.8
176.6
-8.03
-14.78
-7.50
-13.98
0.53
0.80
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-8.00
-8.03
-5.88
0.12
-0.33
-0.53
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-7.06
-5.74
0.84
0.31
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.71
2.76
2.76
2.79
2.77
3.40
3.68
2.73
2.88
0.01
0.00
0.00
-0.01
-0.05
-0.19
0.10
0.03
0.04
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.74
1.74
1.74
1.83
1.76
3.26
3.65
1.75
1.87
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
173.8
171.3
171.3
154.4
169.1
88.8
83.7
176.3
173.9
-8.21
-7.92
0.29
2.62
2.70
0.08
1.94
1.72
159.3
176.2
-4.10
-3.51
-4.27
-3.29
-0.18
0.22
2.82
3.01
2.83
3.08
0.02
0.07
2.12
2.61
1.86
2.37
168.5
123.7
175.3
125.2
-0.66
3.01
3.15
3.08
3.00
0.07
-0.15
2.60
2.42
2.37
1.97
124.0
179.0
125.2
178.2
3.00
2.81
-0.15
0.01
3.64
2.09
3.35
1.83
69.8
176.4
61.6
173.8
H2NH...NH3, linear Cs (33)
-3.38
-4.04
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.61
0.61
3.15
2.80
-7.18
-6.28
0.90
2.77
2.84
0.07
2.06
1.86
170.6
173.1
-7.00
-6.46
0.55
2.79
2.86
0.08
2.03
1.85
177.9
174.9
-7.77
-6.33
-6.31
-6.34
1.46
-0.01
2.73
2.81
2.80
2.85
0.06
0.04
2.10
2.07
1.86
1.83
151.1
168.3
159.4
178.9
-5.89
-5.70
0.20
2.82
2.88
0.06
2.07
1.86
179.5
180.0
-6.63
-11.03
-5.63
-9.02
1.00
2.01
2.77
2.82
2.84
2.98
0.07
0.17
2.12
2.20
1.90
2.09
155.6
143.2
162.1
144.5
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.91
-7.39
0.84
0.56
Vinylamine...OH2 (44)
-3.80
-4.34
-0.54
2.70
2.76
2.88
2.77
3.04
2.80
2.82
2.95
2.86
2.91
0.11
0.06
0.07
0.09
-0.13
2.05
2.11
2.25
2.20
2.20
1.86
1.85
2.01
2.01
1.89
151.5
153.9
145.4
141.1
163.8
158.9
167.1
150.3
143.5
177.7
Bush, Bayly, Halgren 4/5/99 SM B - 10 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.46
0.16
2.94
2.92
-0.02
2.20
1.90
173.4
174.9
-2.93
-2.68
0.25
3.33
3.40
0.07
2.29
2.06
175.3
172.7
-3.56
-3.04
0.52
3.12
3.45
0.34
3.13
2.48
97.9
177.0
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.67
1.11
3.12
3.38
3.45
3.63
0.34
0.26
3.13
2.84
3.83
2.67
97.6
147.0
60.6
172.9
-2.66
-2.95
-0.29
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.79
-0.59
3.59
3.59
4.56
3.72
3.72
4.51
0.13
0.13
-0.05
3.50
3.33
4.27
2.83
3.70
3.70
108.4
121.0
132.4
151.9
83.7
142.5
-0.96
-1.21
-0.25
4.15
4.03
-0.12
3.19
2.71
175.6
167.3
-2.27
-1.84
0.43
3.47
3.51
0.04
2.83
2.57
175.5
163.0
-11.94
-10.25
1.68
2.63
2.71
0.08
1.90
1.72
168.3
170.9
2.98
2.71
2.67
2.90
2.75
0.08
0.08
0.18
0.26
0.09
2.53
1.94
1.83
2.17
2.10
2.32
1.73
1.73
2.29
1.77
119.0
161.0
148.9
124.2
140.6
120.3
177.7
156.9
115.3
177.8
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-8.23
-10.53
2.46
4.96
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.55
2.57
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.48
1.39
2.69
2.70
3.36
2.73
0.67
0.03
2.19
2.06
3.55
1.76
133.1
153.8
71.1
175.5
-3.09
-2.83
-2.91
-2.76
0.17
0.07
3.34
3.04
3.40
3.09
0.06
0.06
2.82
2.36
2.45
2.07
143.6
155.9
163.2
173.5
-19.30
-18.33
0.97
2.70
2.68
-0.02
1.79
1.64
173.7
170.8
-18.48
-18.82
-0.34
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.14
-0.19
2.85
2.85
2.71
2.78
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.4
175.9
-16.98
-17.44
-0.46
2.70
2.63
-0.08
1.91
1.59
148.7
175.4
-19.59
-19.55
0.04
2.83
2.78
-0.05
2.09
1.88
142.6
144.4
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-18.16
1.82
2.83
2.66
2.77
2.70
-0.06
0.04
2.09
1.77
1.87
1.66
142.6
163.4
144.7
179.2
-21.85
-19.50
2.34
2.77
2.78
0.01
2.06
1.92
142.8
144.6
2.78
2.79
0.02
2.08
1.93
141.8
144.6
Bush, Bayly, Halgren 4/5/99 SM B - 11 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 12 -
Table B-IV. __________________________________________________________________________________________________
Unique-bond-LJ12-6 BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-6.74
-0.28
2.73
2.73
0.00
2.03
1.74
172.3
174.1
-5.02
-5.03
-0.01
2.58
2.77
0.19
2.31
2.12
111.8
122.3
-6.11
-6.81
-0.70
2.58
2.72
2.77
2.72
0.19
0.00
2.31
2.01
2.12
1.73
111.8
171.0
122.3
175.3
-6.15
-7.55
-1.40
2.72
2.68
-0.05
2.01
1.68
174.9
179.4
-6.09
-7.79
-1.70
2.71
2.66
-0.05
2.00
1.67
174.5
176.7
-5.84
-4.90
0.95
2.71
2.81
0.10
2.02
1.84
163.8
175.8
-8.10
-8.55
-0.45
2.67
2.70
0.03
1.95
1.73
174.0
164.9
-5.18
-6.21
-1.03
2.79
2.75
-0.05
2.12
1.76
160.8
174.7
-8.18
-9.11
-0.93
2.65
2.66
0.01
1.93
1.67
175.0
179.5
-5.16
-4.00
-17.10
-6.11
-4.22
-16.92
-0.95
-0.22
0.18
2.79
2.78
2.57
2.76
3.30
2.63
-0.03
0.52
0.06
2.11
2.22
1.83
1.79
2.60
1.63
163.2
141.6
175.9
169.3
128.9
173.7
2.57
2.59
2.63
2.68
0.06
0.09
1.83
1.90
1.63
1.69
175.9
158.1
173.7
168.0
2.59
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.68
2.65
2.71
2.97
2.84
2.83
3.30
2.91
2.70
2.85
2.76
0.09
0.11
0.10
0.00
-0.12
-0.08
0.09
0.17
-0.06
0.08
0.05
3.42
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
3.65
1.66
1.99
2.07
2.78
1.91
2.68
1.98
1.72
1.91
1.78
43.9
171.5
122.3
141.0
151.9
155.0
117.5
155.6
167.0
138.7
147.6
3.6
174.0
128.8
152.7
83.5
155.4
122.6
158.3
175.2
162.4
175.6
H3CCOOH...OHH (13)
-11.72
-10.94
0.78
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-10.76
0.47
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-5.24
-0.34
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.48
-0.67
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
-4.72
-7.79
-2.93
-5.25
0.49
-1.40
0.89
0.56
Bush, Bayly, Halgren 4/5/99 SM B - 13 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.90
-6.42
-0.03
-0.45
2.74
2.87
2.71
2.93
-0.03
0.06
2.06
2.12
1.72
1.91
163.2
178.4
177.3
174.9
-8.03
-14.78
-8.49
-15.07
-0.46
-0.29
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-9.54
-8.93
-7.71
-1.42
-1.23
-2.36
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-8.15
-6.25
-0.25
-0.19
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.68
2.82
2.82
2.83
2.85
3.27
3.42
2.69
2.93
-0.02
0.07
0.07
0.03
0.02
-0.32
-0.17
-0.01
0.09
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.69
1.80
1.80
1.87
1.84
3.09
3.29
1.71
1.91
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
177.6
174.1
174.1
155.3
167.8
90.9
88.6
178.9
172.1
-8.21
-9.25
-1.04
2.62
2.65
0.03
1.94
1.66
159.3
177.5
-4.10
-3.51
-5.43
-4.26
-1.33
-0.75
2.82
3.01
2.77
3.00
-0.04
0.00
2.12
2.61
1.79
2.24
168.5
123.7
175.6
130.3
-1.12
3.01
3.15
3.00
3.06
0.00
-0.10
2.60
2.42
2.24
2.02
124.0
179.0
130.2
176.7
3.06
2.78
-0.10
-0.02
3.64
2.09
3.10
1.79
69.8
176.4
77.9
176.7
H2NH...NH3, linear Cs (33)
-3.38
-4.50
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-7.71
-0.49
3.15
2.80
-7.18
-7.54
-0.36
2.77
2.80
0.02
2.06
1.81
170.6
175.9
-7.00
-7.11
-0.10
2.79
2.90
0.11
2.03
1.88
177.9
174.1
-7.77
-6.33
-6.64
-6.98
1.13
-0.65
2.73
2.81
2.84
2.89
0.10
0.08
2.10
2.07
1.85
1.87
151.1
168.3
178.9
178.0
-5.89
-6.31
-0.42
2.82
2.91
0.09
2.07
1.89
179.5
180.0
-6.63
-11.03
-6.20
-10.56
0.44
0.47
2.77
2.82
2.82
2.92
0.04
0.10
2.12
2.20
1.84
1.99
155.6
143.2
170.6
149.9
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-6.72
-8.80
0.02
-0.85
Vinylamine...OH2 (44)
-3.80
-4.78
-0.98
2.70
2.76
2.88
2.77
3.04
2.76
2.81
2.96
2.76
2.95
0.06
0.05
0.08
0.00
-0.10
2.05
2.11
2.25
2.20
2.20
1.78
1.82
2.01
1.84
1.92
151.5
153.9
145.4
141.1
163.8
167.6
179.2
153.7
154.3
179.0
Bush, Bayly, Halgren 4/5/99 SM B - 14 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-5.10
-0.48
2.94
2.95
0.01
2.20
1.93
173.4
178.0
-2.93
-3.47
-0.54
3.33
3.26
-0.07
2.29
1.92
175.3
171.4
-3.56
-4.10
-0.54
3.12
3.18
0.06
3.13
2.20
97.9
179.8
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-3.45
0.33
3.12
3.38
3.18
3.43
0.06
0.06
3.13
2.84
3.53
2.69
97.6
147.0
61.6
133.5
-2.66
-4.48
-1.82
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-3.87
-1.67
3.59
3.59
4.56
3.46
3.46
4.68
-0.13
-0.13
0.12
3.50
3.33
4.27
3.22
2.72
4.07
108.4
121.0
132.4
96.0
133.7
123.6
-0.96
-1.59
-0.62
4.15
3.67
-0.48
3.19
2.35
175.6
167.0
-2.27
-2.45
-0.18
3.47
3.23
-0.24
2.83
2.28
175.5
168.4
-11.94
-11.82
0.12
2.63
2.70
0.07
1.90
1.70
168.3
175.0
2.94
2.65
2.63
2.95
2.69
0.04
0.02
0.14
0.31
0.03
2.53
1.94
1.83
2.17
2.10
2.21
1.66
1.65
2.42
1.70
119.0
161.0
148.9
124.2
140.6
125.4
175.9
167.7
110.4
179.0
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-9.95
-12.03
0.74
3.45
Methylethylhydroxylamine...OH2 (56)
-8.13
-6.76
1.37
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.40
1.47
2.69
2.70
3.28
2.81
0.59
0.11
2.19
2.06
3.42
1.84
133.1
153.8
73.7
173.5
-3.09
-2.83
-3.43
-3.40
-0.34
-0.57
3.34
3.04
3.28
3.06
-0.05
0.02
2.82
2.36
2.33
2.03
143.6
155.9
165.9
179.4
-19.30
-18.42
0.88
2.70
2.81
0.11
1.79
1.77
173.7
172.0
-18.48
-20.20
-1.72
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-16.56
0.39
2.85
2.85
2.71
2.86
2.86
2.81
0.01
0.01
0.10
2.08
2.08
1.81
1.92
1.92
1.78
147.8
147.7
174.5
154.5
154.5
175.9
-16.98
-16.71
0.27
2.70
2.80
0.10
1.91
1.78
148.7
171.4
-19.59
-21.61
-2.02
2.83
2.86
0.02
2.09
1.90
142.6
154.4
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-19.23
0.76
2.83
2.66
2.86
2.79
0.02
0.13
2.09
1.77
1.90
1.75
142.6
163.4
154.4
177.6
-21.85
-22.61
-0.76
2.77
2.69
-0.08
2.06
1.80
142.8
147.0
2.78
2.70
-0.08
2.08
1.81
141.8
146.9
Bush, Bayly, Halgren 4/5/99 SM B - 15 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
Bush, Bayly, Halgren 4/5/99 SM B - 16 -
Consensus BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.72
0.74
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.3
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
-6.11
-5.42
0.69
2.58
2.72
2.82
2.79
0.24
0.07
2.31
2.01
2.24
1.83
111.8
171.0
117.3
166.8
-6.15
-5.49
0.66
2.72
2.77
0.05
2.01
1.79
174.9
178.1
-6.09
-5.31
0.78
2.71
2.77
0.06
2.00
1.79
174.5
178.3
-5.84
-4.85
0.99
2.71
2.84
0.13
2.02
1.89
163.8
165.1
-8.10
-7.06
1.04
2.67
2.74
0.07
1.95
1.77
174.0
167.3
-5.18
-4.22
0.96
2.79
2.88
0.09
2.12
1.95
160.8
159.1
-8.18
-7.24
0.93
2.65
2.72
0.07
1.93
1.74
175.0
176.1
-5.16
-4.00
-17.10
-4.39
-3.02
-13.14
0.77
0.99
3.96
2.79
2.78
2.57
2.88
3.29
2.69
0.09
0.50
0.12
2.11
2.22
1.83
1.94
2.53
1.71
163.2
141.6
175.9
159.1
134.6
167.8
H3CCOOH...OHH (13)
-11.72
-9.20
2.53
2.57
2.59
2.69
2.72
0.12
0.14
1.83
1.90
1.71
1.77
175.9
158.1
167.8
161.6
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.72
1.51
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-5.07
-0.17
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.72b
-5.90
2.59
2.54
2.61
2.97
2.96
2.90
2.72
2.69
2.65
3.01
2.81
2.65
0.14
0.15
0.03
0.04
-0.14
-0.26
3.42
1.80
2.22
2.44
2.35
2.27
3.69
1.70
1.97
2.11
2.72
1.97
43.9
171.5
122.3
141.0
151.9
155.0
7.1
173.7
124.3
153.4
85.4
124.3
1.40
0.47
1.92
0.40
3.21
2.73
2.76
2.78
2.72
4.74
2.96
2.77
2.99
2.76
1.53
0.22
0.01
0.21
0.05
2.95
2.08
2.06
2.24
2.11
5.63
2.04
1.79
2.12
1.79
117.5
155.6
167.0
138.7
147.6
20.9
155.4
177.0
148.4
169.9
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
-3.80
-5.92
-1.90
-5.41
Bush, Bayly, Halgren 4/5/99 SM B - 1 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.06
-6.28
0.81
-0.31
2.74
2.87
2.75
2.86
0.01
0.00
2.06
2.12
1.78
1.84
163.2
178.4
175.2
178.1
-8.03
-14.78
-7.01
-10.69
1.01
4.09
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-6.49
-8.24
-5.58
1.64
-0.54
-0.23
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-6.72
-6.47
1.18
-0.42
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.75
2.84
2.84
2.80
2.80
3.61
3.61
2.76
2.84
0.05
0.08
0.08
0.00
-0.03
0.03
0.03
0.05
0.00
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.77
1.83
1.83
1.78
1.79
3.48
3.48
1.78
1.82
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
172.8
170.9
170.9
175.4
166.4
88.9
88.9
174.2
174.6
-8.21
-7.28
0.93
2.62
2.73
0.11
1.94
1.75
159.3
176.0
-4.10
-3.51
-3.68
-2.98
0.42
0.53
2.82
3.01
2.87
3.11
0.06
0.10
2.12
2.61
1.90
2.40
168.5
123.7
178.0
125.4
-0.23
3.01
3.15
3.11
3.04
0.10
-0.12
2.60
2.42
2.40
2.01
124.0
179.0
125.4
178.1
3.04
2.82
-0.12
0.03
3.64
2.09
3.37
1.84
69.8
176.4
62.7
173.8
H2NH...NH3, linear Cs (33)
-3.38
-3.61
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.28
0.94
3.15
2.80
-7.18
-5.80
1.38
2.77
2.88
0.11
2.06
1.90
170.6
172.7
-7.00
-6.48
0.52
2.79
2.87
0.08
2.03
1.85
177.9
177.1
-7.77
-6.33
-5.86
-5.92
1.91
0.41
2.73
2.81
2.83
2.88
0.09
0.07
2.10
2.07
1.90
1.86
151.1
168.3
156.6
179.0
-5.89
-5.36
0.54
2.82
2.89
0.07
2.07
1.87
179.5
180.0
-6.63
-11.03
-4.99
-8.55
1.64
2.48
2.77
2.82
2.88
3.05
0.11
0.23
2.12
2.20
1.96
2.18
155.6
143.2
157.7
142.2
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-6.50
-6.12
0.24
1.84
Vinylamine...OH2 (44)
-3.80
-4.34
-0.54
2.70
2.76
2.88
2.77
3.04
2.81
2.78
2.98
2.97
2.90
0.11
0.03
0.10
0.20
-0.14
2.05
2.11
2.25
2.20
2.20
1.86
1.81
2.06
2.14
1.87
151.5
153.9
145.4
141.1
163.8
161.4
168.5
147.8
141.6
174.3
Bush, Bayly, Halgren 4/5/99 SM B - 2 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.46
0.17
2.94
2.91
-0.03
2.20
1.88
173.4
172.7
-2.93
-2.61
0.32
3.33
3.41
0.08
2.29
2.07
175.3
172.6
-3.56
-2.81
0.75
3.12
3.45
0.33
3.13
2.48
97.9
172.2
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.50
1.28
3.12
3.38
3.45
3.63
0.33
0.26
3.13
2.84
3.87
2.67
97.6
147.0
57.5
174.5
-2.66
-2.83
-0.17
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.83
-0.63
3.59
3.59
4.56
3.74
3.74
4.33
0.15
0.15
-0.23
3.50
3.33
4.27
2.92
3.59
3.51
108.4
121.0
132.4
142.2
91.1
143.4
-0.96
-1.17
-0.21
4.15
4.04
-0.11
3.19
2.71
175.6
167.2
-2.27
-1.81
0.46
3.47
3.52
0.04
2.83
2.58
175.5
163.0
-11.94
-9.52
2.42
2.63
2.72
0.09
1.90
1.73
168.3
172.3
3.06
2.74
2.69
3.06
2.77
0.17
0.11
0.20
0.42
0.11
2.53
1.94
1.83
2.17
2.10
2.45
1.76
1.74
2.53
1.79
119.0
161.0
148.9
124.2
140.6
117.1
179.2
162.8
110.8
179.1
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-7.75
-9.21
2.94
6.27
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.08
3.05
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.43
1.44
2.69
2.70
3.36
2.74
0.67
0.04
2.19
2.06
3.44
1.77
133.1
153.8
77.2
176.9
-3.09
-2.83
-2.76
-3.02
0.33
-0.20
3.34
3.04
3.36
3.08
0.03
0.05
2.82
2.36
2.42
2.06
143.6
155.9
162.1
174.7
-19.30
-18.43
0.86
2.70
2.68
-0.02
1.79
1.64
173.7
173.5
-18.48
-18.83
-0.35
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.12
-0.17
2.85
2.85
2.71
2.77
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.3
175.9
-16.98
-17.98
-1.01
2.70
2.61
-0.09
1.91
1.58
148.7
176.1
-19.59
-18.95
0.64
2.83
2.79
-0.05
2.09
1.89
142.6
144.5
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-20.19
-0.20
2.83
2.66
2.79
2.64
-0.05
-0.02
2.09
1.77
1.89
1.60
142.6
163.4
144.5
177.6
-21.85
-19.39
2.46
2.77
2.79
0.02
2.06
1.93
142.8
144.5
2.78
2.79
0.01
2.08
1.93
141.8
144.5
Bush, Bayly, Halgren 4/5/99 SM B - 3 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 4 -
Table B-II. _________________________________________________________________________________________________
Single-molecule BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.72
0.74
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.3
-6.11
-5.36
0.75
2.58
2.72
2.82
2.78
0.24
0.06
2.31
2.01
2.24
1.81
111.8
171.0
117.3
168.1
-6.15
-5.58
0.57
2.72
2.77
0.05
2.01
1.79
174.9
179.8
-6.09
-5.37
0.72
2.71
2.76
0.05
2.00
1.78
174.5
177.2
-5.84
-3.98
1.87
2.71
2.90
0.19
2.02
1.95
163.8
165.5
-8.10
-6.33
1.77
2.67
2.77
0.10
1.95
1.80
174.0
167.4
-5.18
-3.87
1.31
2.79
2.91
0.12
2.12
1.98
160.8
157.9
-8.18
-8.12
0.06
2.65
2.69
0.04
1.93
1.70
175.0
176.0
-5.16
-4.00
-17.10
-4.90
-2.93
-15.19
0.26
1.07
1.91
2.79
2.78
2.57
2.84
3.31
2.65
0.05
0.53
0.08
2.11
2.22
1.83
1.90
2.56
1.67
163.2
141.6
175.9
160.7
134.0
168.1
2.57
2.59
2.65
2.74
0.08
0.15
1.83
1.90
1.67
1.79
175.9
158.1
168.1
160.4
2.74
2.71
2.67
3.03
2.82
2.67
0.15
0.17
0.06
0.06
-0.13
-0.23
3.42
1.80
2.22
2.44
2.35
2.27
3.71
1.73
2.00
2.13
2.72
2.00
43.9
171.5
122.3
141.0
151.9
155.0
4.8
172.8
123.5
153.4
86.1
123.5
4.77
2.93
2.74
2.94
2.81
1.56
0.20
-0.01
0.17
0.09
2.95
2.08
2.06
2.24
2.11
5.67
2.01
1.76
1.97
1.84
117.5
155.6
167.0
138.7
147.6
20.4
157.9
175.0
173.2
169.9
H3CCOOH...OHH (13)
-11.72
-9.54
2.18
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.02
2.20
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.73
0.17
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.02b
-5.21
2.59
2.54
2.61
2.97
2.96
2.90
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
-4.02
-6.65
-2.56
-4.61
1.18
-0.26
1.26
1.20
3.21
2.73
2.76
2.78
2.72
Bush, Bayly, Halgren 4/5/99 SM B - 5 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-5.94
-5.61
0.93
0.36
2.74
2.87
2.75
2.90
0.01
0.04
2.06
2.12
1.77
1.88
163.2
178.4
176.0
178.5
-8.03
-14.78
-7.37
-13.04
0.65
1.74
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-8.26
-7.77
-5.98
-0.14
-0.07
-0.63
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-6.88
-5.45
1.02
0.60
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.72
2.78
2.78
2.77
2.80
3.52
3.52
2.75
2.90
0.02
0.02
0.02
-0.03
-0.03
-0.06
-0.06
0.04
0.06
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.75
1.76
1.76
1.80
1.79
3.47
3.47
1.77
1.88
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
173.6
171.7
171.7
155.9
167.1
84.8
84.8
175.7
173.8
-8.21
-7.22
0.99
2.62
2.73
0.11
1.94
1.75
159.3
175.6
-4.10
-3.51
-3.85
-4.02
0.25
-0.51
2.82
3.01
2.87
3.08
0.05
0.07
2.12
2.61
1.90
2.37
168.5
123.7
175.0
125.1
-0.64
3.01
3.15
3.08
3.01
0.07
-0.15
2.60
2.42
2.37
1.97
124.0
179.0
125.1
178.2
3.01
2.81
-0.15
0.01
3.64
2.09
3.34
1.83
69.8
176.4
62.4
173.9
H2NH...NH3, linear Cs (33)
-3.38
-4.02
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.63
0.59
3.15
2.80
-7.18
-5.61
1.57
2.77
2.87
0.10
2.06
1.90
170.6
173.0
-7.00
-6.42
0.58
2.79
2.87
0.08
2.03
1.85
177.9
176.5
-7.77
-6.33
-6.15
-6.15
1.62
0.18
2.73
2.81
2.81
2.86
0.07
0.06
2.10
2.07
1.87
1.84
151.1
168.3
158.6
179.1
-5.89
-5.69
0.20
2.82
2.88
0.06
2.07
1.86
179.5
180.0
-6.63
-11.03
-5.03
-8.59
1.60
2.44
2.77
2.82
2.88
3.02
0.11
0.20
2.12
2.20
1.95
2.14
155.6
143.2
158.5
143.6
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.58
-7.26
1.16
0.69
Vinylamine...OH2 (44)
-3.80
-4.14
-0.34
2.70
2.76
2.88
2.77
3.04
2.81
2.84
2.96
2.86
2.91
0.12
0.08
0.08
0.10
-0.13
2.05
2.11
2.25
2.20
2.20
1.87
1.87
2.04
2.01
1.89
151.5
153.9
145.4
141.1
163.8
160.1
166.7
149.5
144.6
174.3
Bush, Bayly, Halgren 4/5/99 SM B - 6 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.40
0.22
2.94
2.91
-0.03
2.20
1.89
173.4
172.6
-2.93
-2.67
0.26
3.33
3.40
0.07
2.29
2.06
175.3
172.7
-3.56
-3.06
0.50
3.12
3.47
0.35
3.13
2.50
97.9
173.7
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.67
1.12
3.12
3.38
3.47
3.63
0.35
0.25
3.13
2.84
3.88
2.66
97.6
147.0
58.6
172.7
-2.66
-2.95
-0.29
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.84
-0.65
3.59
3.59
4.56
3.72
3.72
4.34
0.13
0.13
-0.22
3.50
3.33
4.27
2.84
3.69
3.53
108.4
121.0
132.4
151.0
84.4
143.3
-0.96
-1.21
-0.24
4.15
4.03
-0.12
3.19
2.71
175.6
167.2
-2.27
-1.84
0.42
3.47
3.51
0.04
2.83
2.57
175.5
163.1
-11.94
-10.18
1.76
2.63
2.71
0.08
1.90
1.72
168.3
170.5
2.97
2.71
2.69
3.06
2.75
0.08
0.08
0.20
0.42
0.09
2.53
1.94
1.83
2.17
2.10
2.31
1.73
1.74
2.53
1.77
119.0
161.0
148.9
124.2
140.6
120.9
177.4
162.8
110.8
178.5
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-8.34
-9.22
2.35
6.26
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.47
2.65
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.49
1.38
2.69
2.70
3.37
2.73
0.68
0.03
2.19
2.06
3.53
1.76
133.1
153.8
72.8
175.5
-3.09
-2.83
-2.72
-2.65
0.37
0.18
3.34
3.04
3.36
3.14
0.03
0.10
2.82
2.36
2.44
2.11
143.6
155.9
158.7
175.4
-19.30
-18.33
0.97
2.70
2.68
-0.02
1.79
1.64
173.7
170.8
-18.48
-18.83
-0.35
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.12
-0.17
2.85
2.85
2.71
2.77
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.3
175.9
-16.98
-17.98
-1.01
2.70
2.61
-0.09
1.91
1.58
148.7
176.1
-19.59
-18.95
0.64
2.83
2.79
-0.05
2.09
1.89
142.6
144.5
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-18.16
1.83
2.83
2.66
2.79
2.70
-0.05
0.04
2.09
1.77
1.89
1.66
142.6
163.4
144.5
179.2
-21.85
-19.49
2.35
2.77
2.79
0.02
2.06
1.92
142.8
144.6
2.78
2.79
0.01
2.08
1.92
141.8
144.6
Bush, Bayly, Halgren 4/5/99 SM B - 7 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 8 -
Table B-III. _________________________________________________________________________________________________
Unique-bond BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-5.71
0.76
2.73
2.79
0.06
2.03
1.82
172.3
170.1
-5.02
-4.25
0.77
2.58
2.82
0.24
2.31
2.24
111.8
117.1
-6.11
-5.85
0.26
2.58
2.72
2.82
2.75
0.24
0.04
2.31
2.01
2.23
1.79
111.8
171.0
117.5
167.9
-6.15
-6.37
-0.22
2.72
2.73
0.01
2.01
1.75
174.9
179.1
-6.09
-6.62
-0.53
2.71
2.69
-0.02
2.00
1.71
174.5
177.6
-5.84
-4.27
1.58
2.71
2.87
0.16
2.02
1.92
163.8
164.7
-8.10
-7.38
0.72
2.67
2.72
0.06
1.95
1.76
174.0
166.3
-5.18
-5.01
0.18
2.79
2.80
0.01
2.12
1.84
160.8
164.2
-8.18
-7.68
0.50
2.65
2.72
0.06
1.93
1.73
175.0
178.1
-5.16
-4.00
-17.10
-5.08
-2.93
-15.14
0.08
1.07
1.97
2.79
2.78
2.57
2.82
3.31
2.65
0.03
0.52
0.08
2.11
2.22
1.83
1.88
2.56
1.67
163.2
141.6
175.9
160.9
134.3
168.1
2.57
2.59
2.65
2.74
0.08
0.15
1.83
1.90
1.67
1.78
175.9
158.1
168.1
160.7
2.74
2.71
2.67
3.03
2.83
2.67
0.15
0.17
0.06
0.06
-0.13
-0.23
3.42
1.80
2.22
2.44
2.35
2.27
3.70
1.73
2.00
2.13
2.72
2.00
43.9
171.5
122.3
141.0
151.9
155.0
5.1
172.7
123.5
153.6
86.3
123.6
4.77
2.92
2.74
2.94
2.81
1.55
0.18
-0.01
0.17
0.09
2.95
2.08
2.06
2.24
2.11
5.67
1.99
1.76
1.97
1.84
117.5
155.6
167.0
138.7
147.6
20.4
157.9
175.0
173.2
170.0
H3CCOOH...OHH (13)
-11.72
-9.57
2.15
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-9.01
2.22
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-4.72
0.18
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-9.01b
-5.21
2.59
2.54
2.61
2.97
2.96
2.90
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
-4.04
-6.67
-2.56
-4.62
1.16
-0.28
1.26
1.19
3.21
2.73
2.76
2.78
2.72
Bush, Bayly, Halgren 4/5/99 SM B - 9 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.06
-5.90
0.81
0.07
2.74
2.87
2.75
2.88
0.00
0.01
2.06
2.12
1.77
1.86
163.2
178.4
176.8
176.6
-8.03
-14.78
-7.50
-13.98
0.53
0.80
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-8.00
-8.03
-5.88
0.12
-0.33
-0.53
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-7.06
-5.74
0.84
0.31
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.71
2.76
2.76
2.79
2.77
3.40
3.68
2.73
2.88
0.01
0.00
0.00
-0.01
-0.05
-0.19
0.10
0.03
0.04
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.74
1.74
1.74
1.83
1.76
3.26
3.65
1.75
1.87
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
173.8
171.3
171.3
154.4
169.1
88.8
83.7
176.3
173.9
-8.21
-7.92
0.29
2.62
2.70
0.08
1.94
1.72
159.3
176.2
-4.10
-3.51
-4.27
-3.29
-0.18
0.22
2.82
3.01
2.83
3.08
0.02
0.07
2.12
2.61
1.86
2.37
168.5
123.7
175.3
125.2
-0.66
3.01
3.15
3.08
3.00
0.07
-0.15
2.60
2.42
2.37
1.97
124.0
179.0
125.2
178.2
3.00
2.81
-0.15
0.01
3.64
2.09
3.35
1.83
69.8
176.4
61.6
173.8
H2NH...NH3, linear Cs (33)
-3.38
-4.04
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-6.61
0.61
3.15
2.80
-7.18
-6.28
0.90
2.77
2.84
0.07
2.06
1.86
170.6
173.1
-7.00
-6.46
0.55
2.79
2.86
0.08
2.03
1.85
177.9
174.9
-7.77
-6.33
-6.31
-6.34
1.46
-0.01
2.73
2.81
2.80
2.85
0.06
0.04
2.10
2.07
1.86
1.83
151.1
168.3
159.4
178.9
-5.89
-5.70
0.20
2.82
2.88
0.06
2.07
1.86
179.5
180.0
-6.63
-11.03
-5.63
-9.02
1.00
2.01
2.77
2.82
2.84
2.98
0.07
0.17
2.12
2.20
1.90
2.09
155.6
143.2
162.1
144.5
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-5.91
-7.39
0.84
0.56
Vinylamine...OH2 (44)
-3.80
-4.34
-0.54
2.70
2.76
2.88
2.77
3.04
2.80
2.82
2.95
2.86
2.91
0.11
0.06
0.07
0.09
-0.13
2.05
2.11
2.25
2.20
2.20
1.86
1.85
2.01
2.01
1.89
151.5
153.9
145.4
141.1
163.8
158.9
167.1
150.3
143.5
177.7
Bush, Bayly, Halgren 4/5/99 SM B - 10 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-4.46
0.16
2.94
2.92
-0.02
2.20
1.90
173.4
174.9
-2.93
-2.68
0.25
3.33
3.40
0.07
2.29
2.06
175.3
172.7
-3.56
-3.04
0.52
3.12
3.45
0.34
3.13
2.48
97.9
177.0
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-2.67
1.11
3.12
3.38
3.45
3.63
0.34
0.26
3.13
2.84
3.83
2.67
97.6
147.0
60.6
172.9
-2.66
-2.95
-0.29
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-2.79
-0.59
3.59
3.59
4.56
3.72
3.72
4.51
0.13
0.13
-0.05
3.50
3.33
4.27
2.83
3.70
3.70
108.4
121.0
132.4
151.9
83.7
142.5
-0.96
-1.21
-0.25
4.15
4.03
-0.12
3.19
2.71
175.6
167.3
-2.27
-1.84
0.43
3.47
3.51
0.04
2.83
2.57
175.5
163.0
-11.94
-10.25
1.68
2.63
2.71
0.08
1.90
1.72
168.3
170.9
2.98
2.71
2.67
2.90
2.75
0.08
0.08
0.18
0.26
0.09
2.53
1.94
1.83
2.17
2.10
2.32
1.73
1.73
2.29
1.77
119.0
161.0
148.9
124.2
140.6
120.3
177.7
156.9
115.3
177.8
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-8.23
-10.53
2.46
4.96
Methylethylhydroxylamine...OH2 (56)
-8.13
-5.55
2.57
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.48
1.39
2.69
2.70
3.36
2.73
0.67
0.03
2.19
2.06
3.55
1.76
133.1
153.8
71.1
175.5
-3.09
-2.83
-2.91
-2.76
0.17
0.07
3.34
3.04
3.40
3.09
0.06
0.06
2.82
2.36
2.45
2.07
143.6
155.9
163.2
173.5
-19.30
-18.33
0.97
2.70
2.68
-0.02
1.79
1.64
173.7
170.8
-18.48
-18.82
-0.34
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-17.14
-0.19
2.85
2.85
2.71
2.78
2.77
2.64
-0.08
-0.08
-0.07
2.08
2.08
1.81
1.86
1.86
1.61
147.8
147.7
174.5
147.3
147.4
175.9
-16.98
-17.44
-0.46
2.70
2.63
-0.08
1.91
1.59
148.7
175.4
-19.59
-19.55
0.04
2.83
2.78
-0.05
2.09
1.88
142.6
144.4
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-18.16
1.82
2.83
2.66
2.77
2.70
-0.06
0.04
2.09
1.77
1.87
1.66
142.6
163.4
144.7
179.2
-21.85
-19.50
2.34
2.77
2.78
0.01
2.06
1.92
142.8
144.6
2.78
2.79
0.02
2.08
1.93
141.8
144.6
Bush, Bayly, Halgren 4/5/99 SM B - 11 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
b Dimer collapses to structure 14.
Bush, Bayly, Halgren 4/5/99 SM B - 12 -
Table B-IV. __________________________________________________________________________________________________
Unique-bond-LJ12-6 BCI vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.
Number)a
Dimer (Structure
HOH...OH2 (1)
HOH...HOH, cyclic Cs (2)
HOH...OHCH3 (3)
CH3OH...OH2 (4)
CH3OH...OHCH3 (5)
HOH...O(CH3)2 (6)
C6H5OH...OH2 (7)
HOH...OHC6H5 (8)
t-Vinyl alcohol...OH2 (9)
HOH...t-Vinyl alcohol (10)
HOH...Furan (11)
H3CCOOH...HOOCCH3, cyclic (12)
Energy (kcal/mol)
SQM
FF
Diff
X...Z distance, Å
SQM
FF
Diff
H...Z distance
SQM
FF
X–H...Z angle
QM
FF
-6.47
-6.74
-0.28
2.73
2.73
0.00
2.03
1.74
172.3
174.1
-5.02
-5.03
-0.01
2.58
2.77
0.19
2.31
2.12
111.8
122.3
-6.11
-6.81
-0.70
2.58
2.72
2.77
2.72
0.19
0.00
2.31
2.01
2.12
1.73
111.8
171.0
122.3
175.3
-6.15
-7.55
-1.40
2.72
2.68
-0.05
2.01
1.68
174.9
179.4
-6.09
-7.79
-1.70
2.71
2.66
-0.05
2.00
1.67
174.5
176.7
-5.84
-4.90
0.95
2.71
2.81
0.10
2.02
1.84
163.8
175.8
-8.10
-8.55
-0.45
2.67
2.70
0.03
1.95
1.73
174.0
164.9
-5.18
-6.21
-1.03
2.79
2.75
-0.05
2.12
1.76
160.8
174.7
-8.18
-9.11
-0.93
2.65
2.66
0.01
1.93
1.67
175.0
179.5
-5.16
-4.00
-17.10
-6.11
-4.22
-16.92
-0.95
-0.22
0.18
2.79
2.78
2.57
2.76
3.30
2.63
-0.03
0.52
0.06
2.11
2.22
1.83
1.79
2.60
1.63
163.2
141.6
175.9
169.3
128.9
173.7
2.57
2.59
2.63
2.68
0.06
0.09
1.83
1.90
1.63
1.69
175.9
158.1
173.7
168.0
2.59
2.54
2.61
2.97
2.96
2.90
3.21
2.73
2.76
2.78
2.72
2.68
2.65
2.71
2.97
2.84
2.83
3.30
2.91
2.70
2.85
2.76
0.09
0.11
0.10
0.00
-0.12
-0.08
0.09
0.17
-0.06
0.08
0.05
3.42
1.80
2.22
2.44
2.35
2.27
2.95
2.08
2.06
2.24
2.11
3.65
1.66
1.99
2.07
2.78
1.91
2.68
1.98
1.72
1.91
1.78
43.9
171.5
122.3
141.0
151.9
155.0
117.5
155.6
167.0
138.7
147.6
3.6
174.0
128.8
152.7
83.5
155.4
122.6
158.3
175.2
162.4
175.6
H3CCOOH...OHH (13)
-11.72
-10.94
0.78
trans,trans-Oxalic acid...OHH, cyclic (14)
-11.23
-10.76
0.47
OHH...cis,cis-Oxalic acid, cyclic (15)
-4.90
-5.24
-0.34
OHH...trans,trans-Oxalic acid, cyclic (16)
-3.82
-4.48
-0.67
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
-4.72
-7.79
-2.93
-5.25
0.49
-1.40
0.89
0.56
Bush, Bayly, Halgren 4/5/99 SM B - 13 -
HOH...Acetone (21)
t-NMA...OH2 (22)
HOH...t-NMA (23)
Formamide dimer, cyclic (24)
-6.87
-5.97
-6.90
-6.42
-0.03
-0.45
2.74
2.87
2.71
2.93
-0.03
0.06
2.06
2.12
1.72
1.91
163.2
178.4
177.3
174.9
-8.03
-14.78
-8.49
-15.07
-0.46
-0.29
Formamide dimer, parallel (25)
t-NMA dimer, antiparallel (26)
t-NMA antiparallel stacked (27)
-8.12
-7.70
-5.35
-9.54
-8.93
-7.71
-1.42
-1.23
-2.36
HOH...N-Methylformamide (28)
N-Methylformamide...OH2 (29)
t-N-OH,N-Meacetamide...OH2 (30)
HOH...t-N-OH,N-Methylacetamide (31)
H2NH...HNH2, cyclic C2h (32)
-7.90
-6.05
-8.15
-6.25
-0.25
-0.19
2.70
2.76
2.76
2.80
2.83
3.58
3.58
2.71
2.84
2.68
2.82
2.82
2.83
2.85
3.27
3.42
2.69
2.93
-0.02
0.07
0.07
0.03
0.02
-0.32
-0.17
-0.01
0.09
2.00
2.00
2.00
2.09
2.08
4.04
4.04
2.01
2.09
1.69
1.80
1.80
1.87
1.84
3.09
3.29
1.71
1.91
167.7
171.5
171.6
156.6
171.8
74.6
74.6
164.8
173.7
177.6
174.1
174.1
155.3
167.8
90.9
88.6
178.9
172.1
-8.21
-9.25
-1.04
2.62
2.65
0.03
1.94
1.66
159.3
177.5
-4.10
-3.51
-5.43
-4.26
-1.33
-0.75
2.82
3.01
2.77
3.00
-0.04
0.00
2.12
2.61
1.79
2.24
168.5
123.7
175.6
130.3
-1.12
3.01
3.15
3.00
3.06
0.00
-0.10
2.60
2.42
2.24
2.02
124.0
179.0
130.2
176.7
3.06
2.78
-0.10
-0.02
3.64
2.09
3.10
1.79
69.8
176.4
77.9
176.7
H2NH...NH3, linear Cs (33)
-3.38
-4.50
HOH...NH3 (34)
HOH...NH2CH3 (35)
Imidazole...OH2 (36)
HOH...Imidazole (37)
Indole...OH2 (38)
Pyrrole...OH2 (39)
HOH...Pyridine (40)
Formamidine...H2O, cyclic (41)
-7.22
-7.71
-0.49
3.15
2.80
-7.18
-7.54
-0.36
2.77
2.80
0.02
2.06
1.81
170.6
175.9
-7.00
-7.11
-0.10
2.79
2.90
0.11
2.03
1.88
177.9
174.1
-7.77
-6.33
-6.64
-6.98
1.13
-0.65
2.73
2.81
2.84
2.89
0.10
0.08
2.10
2.07
1.85
1.87
151.1
168.3
178.9
178.0
-5.89
-6.31
-0.42
2.82
2.91
0.09
2.07
1.89
179.5
180.0
-6.63
-11.03
-6.20
-10.56
0.44
0.47
2.77
2.82
2.82
2.92
0.04
0.10
2.12
2.20
1.84
1.99
155.6
143.2
170.6
149.9
HOH...Formaldehydeimine (42)
Guanidine...OHH (43)
-6.74
-7.96
-6.72
-8.80
0.02
-0.85
Vinylamine...OH2 (44)
-3.80
-4.78
-0.98
2.70
2.76
2.88
2.77
3.04
2.76
2.81
2.96
2.76
2.95
0.06
0.05
0.08
0.00
-0.10
2.05
2.11
2.25
2.20
2.20
1.78
1.82
2.01
1.84
1.92
151.5
153.9
145.4
141.1
163.8
167.6
179.2
153.7
154.3
179.0
Bush, Bayly, Halgren 4/5/99 SM B - 14 -
Aniline...OH2 (45)
HSH...OH2 (46)
HOH...S(CH3)2 (47)
-4.63
-5.10
-0.48
2.94
2.95
0.01
2.20
1.93
173.4
178.0
-2.93
-3.47
-0.54
3.33
3.26
-0.07
2.29
1.92
175.3
171.4
-3.56
-4.10
-0.54
3.12
3.18
0.06
3.13
2.20
97.9
179.8
OHH...CH3SSCH3, cyclic (48)
HOH...Thiophene (49)
-3.78
-3.45
0.33
3.12
3.38
3.18
3.43
0.06
0.06
3.13
2.84
3.53
2.69
97.6
147.0
61.6
133.5
-2.66
-4.48
-1.82
HOH...SHC6H5 (50)
HSH...SH2 (51)
HOH...SH2 (52)
CH3COOH...NH3, bidentate (53)
-2.20
-3.87
-1.67
3.59
3.59
4.56
3.46
3.46
4.68
-0.13
-0.13
0.12
3.50
3.33
4.27
3.22
2.72
4.07
108.4
121.0
132.4
96.0
133.7
123.6
-0.96
-1.59
-0.62
4.15
3.67
-0.48
3.19
2.35
175.6
167.0
-2.27
-2.45
-0.18
3.47
3.23
-0.24
2.83
2.28
175.5
168.4
-11.94
-11.82
0.12
2.63
2.70
0.07
1.90
1.70
168.3
175.0
2.94
2.65
2.63
2.95
2.69
0.04
0.02
0.14
0.31
0.03
2.53
1.94
1.83
2.17
2.10
2.21
1.66
1.65
2.42
1.70
119.0
161.0
148.9
124.2
140.6
125.4
175.9
167.7
110.4
179.0
HOH...PyridineN-oxide (54)
MethylethylamineN-oxide...OHH( 55)
-10.69
-15.48
-9.95
-12.03
0.74
3.45
Methylethylhydroxylamine...OH2 (56)
-8.13
-6.76
1.37
2.89
2.63
2.49
2.64
2.66
HOH...FCH3 (59)
HOH...Chloropropane (58)
H2NH...O(CH3)2 (59)
Methylammonium...OH2 (60)
Guanidinium..OHH (61)
-4.87
-3.40
1.47
2.69
2.70
3.28
2.81
0.59
0.11
2.19
2.06
3.42
1.84
133.1
153.8
73.7
173.5
-3.09
-2.83
-3.43
-3.40
-0.34
-0.57
3.34
3.04
3.28
3.06
-0.05
0.02
2.82
2.36
2.33
2.03
143.6
155.9
165.9
179.4
-19.30
-18.42
0.88
2.70
2.81
0.11
1.79
1.77
173.7
172.0
-18.48
-20.20
-1.72
Imidazolium..OH2 (62)
Formamidinium..OH2 (63)
Formamidinium...OH2, cyclicC2v (64)
-16.95
-16.56
0.39
2.85
2.85
2.71
2.86
2.86
2.81
0.01
0.01
0.10
2.08
2.08
1.81
1.92
1.92
1.78
147.8
147.7
174.5
154.5
154.5
175.9
-16.98
-16.71
0.27
2.70
2.80
0.10
1.91
1.78
148.7
171.4
-19.59
-21.61
-2.02
2.83
2.86
0.02
2.09
1.90
142.6
154.4
Formaldehydeiminium...OH2 (65)
OHH...(-)O2CCH3, bidentate (66)
-19.98
-19.23
0.76
2.83
2.66
2.86
2.79
0.02
0.13
2.09
1.77
1.90
1.75
142.6
163.4
154.4
177.6
-21.85
-22.61
-0.76
2.77
2.69
-0.08
2.06
1.80
142.8
147.0
2.78
2.70
-0.08
2.08
1.81
141.8
146.9
Bush, Bayly, Halgren 4/5/99 SM B - 15 -
a For representational
drawings of the dimer structures, see Figure 1 of: T. A. Halgren, J. Comput. Chem., 17. 520-552 (1996).
Bush, Bayly, Halgren 4/5/99 SM B - 16 -