suppmat1632. 103KB Jun 05 2011 09:30:45 PM
Supplementary Material
TABLE VII. Atomic Charges for Test Suite Molecules
Atom
6-31G RESP
DFT RESP
6-31G RESP
DFT RESP
LP
H1
N
H1
C1
C1
C2
C2
H2
C3
H2
H3
N
LP
C1
H1
C2
H2
C3
H3
Pyridine
-0.547
0.260
0.079
-0.268
0.141
-0.021
0.143
-0.633
0.450
0.011
-0.438
0.160
0.190
0.077
0.149
-0.448
0.071
0.120
-0.235
0.147
-0.052
0.146
0.592
-0.727
-0.012
0.109
-0.208
0.133
-0.023
0.112
0.237
-0.503
0.161
-0.010
-0.215
0.643
-0.739
0.159
-0.149
-0.132
H2
N2
H3
C3
C4
H4
N1
LP
C1
H1
N2
-0.506
0.127
0.145
-0.162
H1
C1
N1
Imidazole
-0.490
0.087
0.155
-0.117
LP
H2
0.287
0.262
0.319
0.286
C3
-0.318
-0.327
-0.288
-0.254
H3
0.204
0.184
0.210
0.181
C4
0.104
0.165
-0.065
-0.150
H4
0.118
0.081
0.153
0.155
0.114
0.403
-0.423
-0.579
LP2
H2
O
C2
C3
N
H3
Oxazole
N
LP1
-0.545
-
H1
C1
LP1
-0.513
-
C1
0.438
0.400
0.172
0.179
H1
0.077
0.052
0.051
-0.122
O
-0.234
-0.178
0.458
0.686
-0.439
-0.535
LP2
-
-
C2
-0.139
-0.140
-0.327
-0.375
H2
0.190
0.167
0.237
0.228
C3
0.080
0.109
-0.008
-0.042
H3
0.134
0.104
0.165
0.156
-0.090
-0.034
LP
H3
N
C
H1
H2
Methanimine
N
LP
-0.711
-
-0.658
-0.393
-0.391
C
0.216
0.249
-
0.011
0.021
H1
0.038
0.003
0.072
0.046
H2
0.075
0.056
0.128
0.117
H3
0.382
0.350
0.273
0.241
0.214
-0.473
-0.056
0.115
0.067
0.009
0.041
0.667
-0.732
-0.228
0.156
0.071
-0.093
0.053
0.275
-0.010
-0.048
-0.216
0.248
-0.020
0.031
-0.259
H
LP
C2
H
N
H
C1
H1
N
LP
C1
H1
H2
C2
H
-0.480
0.167
0.056
0.046
0.074
0.046
H2
Methyliminomethane
-0.486
0.217
0.035
0.001
0.193
0.013
H
H
C
N
LP
0.243
0.113
-0.356
-
C
N
LP
Hydrogen Cyanide
0.201
0.144
-0.345
-
LP
N
H
H
H
Ammonia
N
-1.100
H
0.367
LP
a Charge constraint removed
-0.905
0.302
-
0.000(-1.076)a
0.189( 0.363)a
-0.566(-0.013)a
0.000(-1.681)a
0.154( 0.425)a
-0.461( 0.407)a
LP
H1
N
C
H2
H1
H2
H1
N
LP
-0.994
-
Methylamine
-0.912
-
-0.018
-0.538
-0.075
-0.453
H2
0.370
0.338
0.204
0.192
C
0.309
0.292
0.225
0.232
-0.018
-0.019
-0.026
-0.029
0.140
0.699
-0.521
-0.791
H1
LP
H1
H1
N
C
C
H1
H1
H2
H1
H1
Dimethylamine
N
LP
H2
C
H1
-0.692
-0.639
-
-
0.373
0.354
0.240
0.141
-0.010
-0.016
-0.054
-0.198
0.057
0.053
0.042
0.058
0.279
1.103
-0.454
-0.922
LP
H
H
N
C
H
H
C
H
C
H
H
H
H
Trimethylamine
N
LP
-0.330
-0.202
-
-
C
-0.109
-0.177
-0.024
-0.076
H
0.073
0.081
0.027
0.005
-0.099
-0.097
-0.181
-0.157
H H1
LP
O
C
H
O
LP
H1
C
-0.551
-
LP
H
Methanol
-0.497
-
0.368
0.334
0.310
0.280
-0.022
0.006
-0.024
-0.014
H
0.068
0.052
H
H
0.048
LP
H
O
C
H
H
0.058
LP
H
Dimethyl Ether
C
0.028
-0.010
0.035
-0.129
H
0.051
0.050
0.038
0.048
O
-0.366
-0.282
0.081
1.046
-0.191
-0.536
-0.025
0.223
-0.177
-0.254
LP
-
-
LP
LP
O
C
H
H
Formaldehyde
O
LP
-0.454
-0.394
-
-
C
0.426
0.412
0.298
0.228
H
0.014
-0.009
0.040
0.029
0.366
0.322
-0.377
-0.331
LP
O
H1
C1
C2
H2
O
LP
-0.190
-
C1
C2
Furan
-0.167
-
H1
H2
C1
-0.007
-0.007
-0.141
-0.124
H1
0.148
0.130
0.182
0.160
C2
-0.204
-0.179
-0.209
-0.184
H2
0.158
0.139
LP2
0.173
0.152
-0.050
-0.014
LP1
O
C
H
H1
N
H2
Formamide
O
-0.567
-0.509
LP1
-
-
-0.277
-0.253
LP2
-
-
-0.124
-0.143
C
0.638
0.577
0.422
0.411
H
0.026
-0.005
0.087
0.039
N
-0.908
-0.826
-0.823
-0.786
H1
0.420
0.401
0.386
0.383
H2
0.390
0.361
0.379
0.362
-0.165
-0.238
LP2
LP1
O
H
C2
H1
C1
N
H
H2
H
Acetamide
O
-0.610
-0.574
LP1
-
-
-0.209
-0.153
LP2
-
-
-0.153
-0.121
C1
-0.303
-0.444
-0.286
-0.425
H
0.089
0.121
0.091
0.120
C2
0.813
0.810
0.688
0.715
N
-1.014
-0.962
-0.984
-0.938
H1
0.432
0.413
0.420
0.403
H2
0.413
0.396
0.417
0.397
LP2
LP1
O
H1
H3 H
3
C2
C3
C1
N
H1
H2
H1
H3
N-Methyl Acetamide
O
-0.570
-0.528
-0.040
0.053
LP1
-
-
-0.259
-0.288
LP2
-
-
-0.174
-0.188
C1
-0.155
-0.340
-0.148
-0.328
H1
0.046
0.089
0.052
0.093
C2
0.627
0.615
0.493
0.476
N
-0.446
-0.374
-0.434
-0.365
H2
0.299
0.270
0.307
0.280
C3
-0.304
-0.369
-0.296
-0.362
H3
0.137
0.152
0.133
0.148
-0.057
-0.050
-0.145
-0.128
LP
H H1
S
C
H
H
LP
Methanethiol
S
LP
H1
-0.305
-
-0.269
-
0.176
0.155
0.188
0.166
C
-0.200
-0.176
-0.043
-0.038
H
0.110
0.097
0.067
0.059
0.028
0.024
-0.145
-0.128
0.129
0.113
0.001
0.001
0.400
0.352
-0.229
-0.202
-0.339
-0.299
LP
H
H
H
C
H
H
H
S
LP
Dimethylsul de
S
LP
-0.211
-
-0.185
-
C
-0.238
-0.209
H
0.114
0.101
LP
LP
S
C
H
H
Methanethial
S
LP
C
-0.204
-0.056
-0.179
-0.049
H
0.130
0.114
0.199
0.175
0.325
0.286
-0.112
-0.112
LP
C2
H2
S
LP
0.014
-
S
C1
H1
LP
Thiophene
0.013
-
C1
-0.249
-0.219
-0.307
-0.270
H1
0.220
0.193
0.229
0.201
C2
-0.130
-0.115
-0.129
-0.114
H2
0.152
0.134
0.157
0.138
TABLE VIII. Total Energy of Monomer Dataa
System
pyridine
imidazole
oxazole
methanimine
methyliminomethane
hydrogen cyanide
ammonia
Model
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
E(tot)
-246.69582
-247.48038
-10.05
-59.27
+8.48
+7.81
-224.81443
-225.51613
-0.33
-1.55
+8.46
-2.57
-244.63297
-245.34580
+5.31
+3.35
-30.78
-65.78
-94.02846
-94.31337
+4.25
+1.81
-4.22
-4.14
-133.06149
-133.47698
+4.45
+1.31
-12.80
-31.12
-92.87520
-93.15451
0.00
0.00
-6.27
-6.81
-56.18436
-56.35369
0.00
methylamine
dimethylamine
trimethylamine
water
methanol
dimethyl ether
formaldehyde
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
0.00
0.00
0.00
-95.20983
-95.50584
-4.40
-4.88
+1.72
+1.11
-134.23885
-134.66444
+16.96
+14.28
-8.61
-34.85
-173.26930
-173.82759
+3.30
-5.02
-10.48
-11.52
-76.01075
-76.19599
0.00
0.00
0.00
0.00
-115.03542
-115.34494
+5.65
+4.23
-2.89
-3.71
-154.06475
-154.50208
+4.65
+3.38
-5.32
-3.32
-113.86633
-114.16531
0.00
furan
formamide
acetamide
N-methyl acetamide
methanethiol
dimethyl thioether
methanethial
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
0.00
-3.64
-4.23
-228.62521
-229.30748
+2.51
+1.79b
+1.20
0.00
-168.93070
-169.39193
-40.84
-37.42
+4.06
+5.06
-207.97596
-208.56644
-91.58
-105.11
-33.02
-56.36
-247.00601
-247.72662
+0.30
-8.33
+27.49
+27.67
-437.70032
-437.95235
+6.90
+5.28
-1.12
-0.54
-476.73533
-477.12066
+0.13
+0.10
+4.03
+3.93
-436.50646
-436.75457
0.00
thiophene
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
a ab initio energies in hartrees, molecular mechanics energies in kcal/mol
b Scaled 6-31G charges
0.00
-5.02
-3.91
-551.29035
-551.92282
-1.08
-1.18
+22.40
+24.16
TABLE IX. Interaction Energy Dataa
System
pyridine HOH
:::
imidazole HOH
:::
oxazole HOH (N - acceptor)
:::
oxazole HOH (O - acceptor)
:::
methanimine HOH
:::
methyliminomethane HOH
:::
hydrogen cyanide HOH
:::
Model
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4/TIP4P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
E(Form I)
-5.65
-7.61
-5.25
-5.56
-4.93
-7.18
-7.48
-6.53
-8.37
-6.11
-5.40
-8.58
-8.00
-5.23
-6.74
-5.20
-4.42
-6.87
-7.77
-2.24
-3.29
-2.71
-2.08
-3.75
-3.78
-5.65
-7.10
-6.46
-5.99
-7.95
-7.05
-5.67
-7.46
-5.37
-5.06
-7.06
-7.17
-3.62
-4.51
E(Form II)
-2.34
-3.67
-4.81
-5.04
-4.29
-3.67
-2.04
-3.72
-5.34
-6.33
-5.98
-5.06
-3.28
-2.26
-3.56
-4.35
-3.98
-3.53
-2.64
-0.49
-1.52
-1.42
-1.29
-0.92
-0.56
-2.73
-3.57
-4.98
-4.44
-4.12
-3.30
-2.41
-3.65
-4.84
-4.35
-3.79
-2.56
-2.38
-2.98
E(I II)
-3.31
-3.94
-0.44
-0.52
-0.64
-3.51
-5.44
-2.81
-3.03
+0.22
+0.58
-3.52
-4.72
-2.97
-3.18
-0.85
-0.44
-3.34
-5.13
-1.75
-1.77
-1.28
-0.79
-2.83
-3.22
-2.92
-3.53
-1.48
-1.55
-3.83
-3.75
-3.26
-3.81
-0.53
-0.71
-3.27
-4.61
-1.24
-1.53
ammonia HOH
:::
methylamine HOH
:::
dimethylamine HOH
:::
trimethylamine HOH
:::
methanol HOH
:::
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
AMBER 4 LP/TIP3P c
AMBER 4 POL-LP/POL3 c
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
-3.60
-3.21
-4.59
-4.27
-6.30
-7.96
-7.65
-6.31
-7.62
-5.37
-8.66
-6.42
-6.42
-8.44
-7.63
-7.80
-8.75
-7.52
-6.14
-8.59
-6.75
-5.60
-8.11
-7.34
-5.82
-8.60
-4.77
-4.17
-5.68
-4.64
-5.53
-5.53
-5.14
-7.22
-7.22
-6.51
-5.89
-5.89
-5.32
-4.65
-4.65
-4.39
-3.79
-3.25
-3.48
-2.77
-2.77
-3.90
-5.35
-4.15
-5.06
-4.86
-3.79
-2.75
-2.35
-3.54
-4.65
-4.49
-3.70
-3.17
-0.59
-1.46
-1.65
-1.53
-1.51
-0.80
-0.32
-1.11
-1.37
-1.29
-1.30
-0.51
-5.14
-4.24
-4.24
-6.51
-6.46
-6.46
-5.32
-4.49
-4.49
-4.39
-3.55
-3.55
+0.19
+0.04
-1.11
-1.50
-3.53
-4.06
-2.30
-2.16
-2.56
-0.51
-4.87
-3.67
-4.07
-4.90
-2.98
-3.31
-5.05
-4.35
-5.55
-7.13
-5.10
-4.07
-6.60
-6.54
-5.50
-7.49
-3.40
-2.88
-4.38
-4.13
-0.39
-1.29
-0.90
-0.71
-0.76
-0.05
-0.57
-1.40
-0.83
-0.34
-1.10
-0.74
dimethyl ether HOH
:::
formaldehyde HOH
:::
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
-6.78
-6.78
-6.43
-5.69
-5.69
-5.45
-5.27
-5.27
-5.04
-7.10
-7.10
-6.61
-4.92
-4.92
-4.33
-4.12
-4.12
-3.52
-5.12
-5.12
-4.87
-4.08
-4.08
-3.83
-4.69
-4.69
-3.57
-5.73
-5.73
-4.14
-5.19
-5.19
-4.83
-4.23
-4.23
-4.01
-5.66
-5.66
-5.12
-4.61
-4.61
-4.18
-6.43
-5.26
-5.26
-5.45
-4.26
-4.26
-5.04
-3.86
-3.86
-6.61
-6.31
-6.31
-4.33
-4.05
-4.05
-3.52
-3.48
-3.48
-4.87
-4.11
-4.11
-3.83
-3.17
-3.17
-3.57
-2.23
-2.23
-4.14
-2.61
-2.61
-4.83
-4.16
-4.16
-4.01
-3.24
-3.24
-5.12
-3.69
-3.69
-4.18
-2.45
-2.45
-0.35
-1.52
-1.17
-0.24
-1.43
-1.19
-0.23
-1.41
-1.18
-0.51
-0.79
-0.30
-0.59
-0.87
-0.28
-0.60
-0.64
-0.04
-0.25
-1.01
-0.76
-0.25
-0.91
-0.66
-1.12
-2.46
-1.34
-1.59
-3.12
-1.53
-0.36
-1.03
-0.67
-0.22
-0.99
-0.77
-0.54
-1.97
-1.43
-0.43
-2.16
-1.73
furan HOH
:::
formamide formamideb
:::
formamide HOH
:::
acetamide HOH
:::
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
-3.04
-4.20
-3.00
-2.34
-4.30
-3.30
-6.16
-7.12
-6.74
-4.94
-7.26
-5.28
-6.86
-6.86
-5.23
-8.63
-8.63
-6.02
-6.99
-6.99
-6.44
-4.97
-4.97
-5.17
-8.71
-8.71
-6.98
-6.03
-6.03
-5.06
-7.02
-7.02
-5.52
-8.87
-8.87
-6.44
-7.69
-7.69
-7.27
-6.03
-6.03
-5.62
-2.09
-3.38
-3.63
-3.48
-2.87
-2.48
-2.74
-4.88
-4.70
-4.04
-4.48
-3.52
-5.23
-4.02
-4.02
-6.02
-5.09
-5.09
-6.44
-5.84
-5.84
-5.17
-5.03
-5.03
-6.98
-5.21
-5.21
-5.06
-4.00
-4.00
-5.52
-4.65
-4.65
-6.44
-6.18
-6.18
-7.27
-6.16
-6.16
-5.62
-5.52
-5.52
-0.95
-0.82
+0.63
+1.14
-1.43
-0.82
-3.42
-2.24
-2.04
-0.90
-2.78
-1.76
-1.63
-2.84
-1.21
-2.61
-3.54
-0.93
-0.55
-1.15
-0.60
+0.20
+0.06
-0.14
-1.73
-3.50
-1.77
-0.97
-2.03
-1.06
-1.50
-2.37
-0.87
-2.43
-2.69
-0.26
-0.42
-1.53
-1.11
-0.41
-0.51
-0.10
N-methyl acetamide HOH
:::
methanethiol HOH
:::
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
-8.72
-8.72
-7.66
-6.31
-6.31
-5.46
-7.26
-7.26
-5.74
-9.09
-9.09
-7.60
-7.61
-7.61
-7.26
-6.71
-6.71
-6.31
-8.91
-8.91
-7.70
-7.56
-7.56
-6.19
-2.57
-2.57
-1.46
-3.48
-3.48
-2.08
-3.76
-3.76
-2.79
-3.26
-3.26
-2.49
-4.34
-4.34
-2.99
-3.59
-3.59
-2.03
-7.66
-5.57
-5.57
-5.46
-4.45
-4.45
-5.74
-5.30
-5.30
-7.60
-6.73
-6.73
-7.26
-6.75
-6.75
-6.31
-5.94
-5.94
-7.70
-5.97
-5.97
-6.19
-4.48
-4.48
-1.46
-2.47
-2.47
-2.08
-3.39
-3.39
-2.79
-3.25
-3.25
-2.49
-2.83
-2.83
-2.99
-4.28
-4.28
-2.03
-3.61
-3.61
-1.06
-3.15
-2.09
-0.85
-1.86
-1.01
-1.52
-1.96
-0.44
-1.49
-2.36
-0.87
-0.35
-0.86
-0.51
-0.40
-0.77
-0.37
-1.21
-2.94
-1.73
-1.37
-3.08
-1.71
-1.11
-0.10
+1.01
-1.40
-0.09
+1.31
-0.97
-0.51
+0.44
-0.77
-0.43
+0.34
-1.35
-0.06
+1.29
-1.56
+0.02
+1.58
dimethyl thioether HOH
:::
methanethial HOH
:::
thiophene HOH
:::
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
-2.92
-2.92
-1.80
-3.97
-3.97
-2.56
-1.54
-1.54
-1.23
-1.49
-1.49
-1.15
-3.67
-3.67
-2.07
-3.13
-3.13
-1.58
-2.39
-2.39
-0.53
-3.10
-3.10
-0.78
-2.76
-2.76
-1.90
-2.40
-2.40
-1.71
-3.02
-3.02
-2.04
-2.52
-2.52
-1.74
-0.89
-1.35
-0.95
-0.76
-1.09
-0.81
-1.80
-2.85
-2.85
-2.56
-3.97
-3.97
-1.23
-1.51
-1.51
-1.15
-1.48
-1.48
-2.07
-3.66
-3.66
-1.58
-3.12
-3.12
-0.53
-0.86
-0.86
-0.78
-1.02
-1.02
-1.90
-2.43
-2.43
-1.71
-2.18
-2.18
-2.04
-2.10
-2.10
-1.74
-1.80
-1.80
-1.38
-1.83
-1.87
-1.83
-1.99
-1.80
-1.12
-0.07
+1.05
-1.41
0.00
+1.41
-0.31
-0.03
+0.28
-0.34
-0.01
+0.33
-1.60
-0.01
+1.59
-1.55
-0.01
+1.54
-1.86
-1.53
+0.33
-2.32
-2.08
+0.24
-0.86
-0.33
+0.53
-0.69
-0.22
+0.47
-0.98
-0.92
+0.06
-0.78
-0.72
+0.06
+0.49
+0.48
+0.92
+1.07
+0.90
+0.99
a
All energies in kcal
mol
b
Structure constrained to single h-bond conformation
cq
(N) = 0 to insure negative charge on lone-pair
TABLE VII. Atomic Charges for Test Suite Molecules
Atom
6-31G RESP
DFT RESP
6-31G RESP
DFT RESP
LP
H1
N
H1
C1
C1
C2
C2
H2
C3
H2
H3
N
LP
C1
H1
C2
H2
C3
H3
Pyridine
-0.547
0.260
0.079
-0.268
0.141
-0.021
0.143
-0.633
0.450
0.011
-0.438
0.160
0.190
0.077
0.149
-0.448
0.071
0.120
-0.235
0.147
-0.052
0.146
0.592
-0.727
-0.012
0.109
-0.208
0.133
-0.023
0.112
0.237
-0.503
0.161
-0.010
-0.215
0.643
-0.739
0.159
-0.149
-0.132
H2
N2
H3
C3
C4
H4
N1
LP
C1
H1
N2
-0.506
0.127
0.145
-0.162
H1
C1
N1
Imidazole
-0.490
0.087
0.155
-0.117
LP
H2
0.287
0.262
0.319
0.286
C3
-0.318
-0.327
-0.288
-0.254
H3
0.204
0.184
0.210
0.181
C4
0.104
0.165
-0.065
-0.150
H4
0.118
0.081
0.153
0.155
0.114
0.403
-0.423
-0.579
LP2
H2
O
C2
C3
N
H3
Oxazole
N
LP1
-0.545
-
H1
C1
LP1
-0.513
-
C1
0.438
0.400
0.172
0.179
H1
0.077
0.052
0.051
-0.122
O
-0.234
-0.178
0.458
0.686
-0.439
-0.535
LP2
-
-
C2
-0.139
-0.140
-0.327
-0.375
H2
0.190
0.167
0.237
0.228
C3
0.080
0.109
-0.008
-0.042
H3
0.134
0.104
0.165
0.156
-0.090
-0.034
LP
H3
N
C
H1
H2
Methanimine
N
LP
-0.711
-
-0.658
-0.393
-0.391
C
0.216
0.249
-
0.011
0.021
H1
0.038
0.003
0.072
0.046
H2
0.075
0.056
0.128
0.117
H3
0.382
0.350
0.273
0.241
0.214
-0.473
-0.056
0.115
0.067
0.009
0.041
0.667
-0.732
-0.228
0.156
0.071
-0.093
0.053
0.275
-0.010
-0.048
-0.216
0.248
-0.020
0.031
-0.259
H
LP
C2
H
N
H
C1
H1
N
LP
C1
H1
H2
C2
H
-0.480
0.167
0.056
0.046
0.074
0.046
H2
Methyliminomethane
-0.486
0.217
0.035
0.001
0.193
0.013
H
H
C
N
LP
0.243
0.113
-0.356
-
C
N
LP
Hydrogen Cyanide
0.201
0.144
-0.345
-
LP
N
H
H
H
Ammonia
N
-1.100
H
0.367
LP
a Charge constraint removed
-0.905
0.302
-
0.000(-1.076)a
0.189( 0.363)a
-0.566(-0.013)a
0.000(-1.681)a
0.154( 0.425)a
-0.461( 0.407)a
LP
H1
N
C
H2
H1
H2
H1
N
LP
-0.994
-
Methylamine
-0.912
-
-0.018
-0.538
-0.075
-0.453
H2
0.370
0.338
0.204
0.192
C
0.309
0.292
0.225
0.232
-0.018
-0.019
-0.026
-0.029
0.140
0.699
-0.521
-0.791
H1
LP
H1
H1
N
C
C
H1
H1
H2
H1
H1
Dimethylamine
N
LP
H2
C
H1
-0.692
-0.639
-
-
0.373
0.354
0.240
0.141
-0.010
-0.016
-0.054
-0.198
0.057
0.053
0.042
0.058
0.279
1.103
-0.454
-0.922
LP
H
H
N
C
H
H
C
H
C
H
H
H
H
Trimethylamine
N
LP
-0.330
-0.202
-
-
C
-0.109
-0.177
-0.024
-0.076
H
0.073
0.081
0.027
0.005
-0.099
-0.097
-0.181
-0.157
H H1
LP
O
C
H
O
LP
H1
C
-0.551
-
LP
H
Methanol
-0.497
-
0.368
0.334
0.310
0.280
-0.022
0.006
-0.024
-0.014
H
0.068
0.052
H
H
0.048
LP
H
O
C
H
H
0.058
LP
H
Dimethyl Ether
C
0.028
-0.010
0.035
-0.129
H
0.051
0.050
0.038
0.048
O
-0.366
-0.282
0.081
1.046
-0.191
-0.536
-0.025
0.223
-0.177
-0.254
LP
-
-
LP
LP
O
C
H
H
Formaldehyde
O
LP
-0.454
-0.394
-
-
C
0.426
0.412
0.298
0.228
H
0.014
-0.009
0.040
0.029
0.366
0.322
-0.377
-0.331
LP
O
H1
C1
C2
H2
O
LP
-0.190
-
C1
C2
Furan
-0.167
-
H1
H2
C1
-0.007
-0.007
-0.141
-0.124
H1
0.148
0.130
0.182
0.160
C2
-0.204
-0.179
-0.209
-0.184
H2
0.158
0.139
LP2
0.173
0.152
-0.050
-0.014
LP1
O
C
H
H1
N
H2
Formamide
O
-0.567
-0.509
LP1
-
-
-0.277
-0.253
LP2
-
-
-0.124
-0.143
C
0.638
0.577
0.422
0.411
H
0.026
-0.005
0.087
0.039
N
-0.908
-0.826
-0.823
-0.786
H1
0.420
0.401
0.386
0.383
H2
0.390
0.361
0.379
0.362
-0.165
-0.238
LP2
LP1
O
H
C2
H1
C1
N
H
H2
H
Acetamide
O
-0.610
-0.574
LP1
-
-
-0.209
-0.153
LP2
-
-
-0.153
-0.121
C1
-0.303
-0.444
-0.286
-0.425
H
0.089
0.121
0.091
0.120
C2
0.813
0.810
0.688
0.715
N
-1.014
-0.962
-0.984
-0.938
H1
0.432
0.413
0.420
0.403
H2
0.413
0.396
0.417
0.397
LP2
LP1
O
H1
H3 H
3
C2
C3
C1
N
H1
H2
H1
H3
N-Methyl Acetamide
O
-0.570
-0.528
-0.040
0.053
LP1
-
-
-0.259
-0.288
LP2
-
-
-0.174
-0.188
C1
-0.155
-0.340
-0.148
-0.328
H1
0.046
0.089
0.052
0.093
C2
0.627
0.615
0.493
0.476
N
-0.446
-0.374
-0.434
-0.365
H2
0.299
0.270
0.307
0.280
C3
-0.304
-0.369
-0.296
-0.362
H3
0.137
0.152
0.133
0.148
-0.057
-0.050
-0.145
-0.128
LP
H H1
S
C
H
H
LP
Methanethiol
S
LP
H1
-0.305
-
-0.269
-
0.176
0.155
0.188
0.166
C
-0.200
-0.176
-0.043
-0.038
H
0.110
0.097
0.067
0.059
0.028
0.024
-0.145
-0.128
0.129
0.113
0.001
0.001
0.400
0.352
-0.229
-0.202
-0.339
-0.299
LP
H
H
H
C
H
H
H
S
LP
Dimethylsul de
S
LP
-0.211
-
-0.185
-
C
-0.238
-0.209
H
0.114
0.101
LP
LP
S
C
H
H
Methanethial
S
LP
C
-0.204
-0.056
-0.179
-0.049
H
0.130
0.114
0.199
0.175
0.325
0.286
-0.112
-0.112
LP
C2
H2
S
LP
0.014
-
S
C1
H1
LP
Thiophene
0.013
-
C1
-0.249
-0.219
-0.307
-0.270
H1
0.220
0.193
0.229
0.201
C2
-0.130
-0.115
-0.129
-0.114
H2
0.152
0.134
0.157
0.138
TABLE VIII. Total Energy of Monomer Dataa
System
pyridine
imidazole
oxazole
methanimine
methyliminomethane
hydrogen cyanide
ammonia
Model
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
E(tot)
-246.69582
-247.48038
-10.05
-59.27
+8.48
+7.81
-224.81443
-225.51613
-0.33
-1.55
+8.46
-2.57
-244.63297
-245.34580
+5.31
+3.35
-30.78
-65.78
-94.02846
-94.31337
+4.25
+1.81
-4.22
-4.14
-133.06149
-133.47698
+4.45
+1.31
-12.80
-31.12
-92.87520
-93.15451
0.00
0.00
-6.27
-6.81
-56.18436
-56.35369
0.00
methylamine
dimethylamine
trimethylamine
water
methanol
dimethyl ether
formaldehyde
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
0.00
0.00
0.00
-95.20983
-95.50584
-4.40
-4.88
+1.72
+1.11
-134.23885
-134.66444
+16.96
+14.28
-8.61
-34.85
-173.26930
-173.82759
+3.30
-5.02
-10.48
-11.52
-76.01075
-76.19599
0.00
0.00
0.00
0.00
-115.03542
-115.34494
+5.65
+4.23
-2.89
-3.71
-154.06475
-154.50208
+4.65
+3.38
-5.32
-3.32
-113.86633
-114.16531
0.00
furan
formamide
acetamide
N-methyl acetamide
methanethiol
dimethyl thioether
methanethial
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
0.00
-3.64
-4.23
-228.62521
-229.30748
+2.51
+1.79b
+1.20
0.00
-168.93070
-169.39193
-40.84
-37.42
+4.06
+5.06
-207.97596
-208.56644
-91.58
-105.11
-33.02
-56.36
-247.00601
-247.72662
+0.30
-8.33
+27.49
+27.67
-437.70032
-437.95235
+6.90
+5.28
-1.12
-0.54
-476.73533
-477.12066
+0.13
+0.10
+4.03
+3.93
-436.50646
-436.75457
0.00
thiophene
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER 4/POL
AMBER 4/LP
AMBER 4/POL-LP
a ab initio energies in hartrees, molecular mechanics energies in kcal/mol
b Scaled 6-31G charges
0.00
-5.02
-3.91
-551.29035
-551.92282
-1.08
-1.18
+22.40
+24.16
TABLE IX. Interaction Energy Dataa
System
pyridine HOH
:::
imidazole HOH
:::
oxazole HOH (N - acceptor)
:::
oxazole HOH (O - acceptor)
:::
methanimine HOH
:::
methyliminomethane HOH
:::
hydrogen cyanide HOH
:::
Model
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4/TIP4P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
E(Form I)
-5.65
-7.61
-5.25
-5.56
-4.93
-7.18
-7.48
-6.53
-8.37
-6.11
-5.40
-8.58
-8.00
-5.23
-6.74
-5.20
-4.42
-6.87
-7.77
-2.24
-3.29
-2.71
-2.08
-3.75
-3.78
-5.65
-7.10
-6.46
-5.99
-7.95
-7.05
-5.67
-7.46
-5.37
-5.06
-7.06
-7.17
-3.62
-4.51
E(Form II)
-2.34
-3.67
-4.81
-5.04
-4.29
-3.67
-2.04
-3.72
-5.34
-6.33
-5.98
-5.06
-3.28
-2.26
-3.56
-4.35
-3.98
-3.53
-2.64
-0.49
-1.52
-1.42
-1.29
-0.92
-0.56
-2.73
-3.57
-4.98
-4.44
-4.12
-3.30
-2.41
-3.65
-4.84
-4.35
-3.79
-2.56
-2.38
-2.98
E(I II)
-3.31
-3.94
-0.44
-0.52
-0.64
-3.51
-5.44
-2.81
-3.03
+0.22
+0.58
-3.52
-4.72
-2.97
-3.18
-0.85
-0.44
-3.34
-5.13
-1.75
-1.77
-1.28
-0.79
-2.83
-3.22
-2.92
-3.53
-1.48
-1.55
-3.83
-3.75
-3.26
-3.81
-0.53
-0.71
-3.27
-4.61
-1.24
-1.53
ammonia HOH
:::
methylamine HOH
:::
dimethylamine HOH
:::
trimethylamine HOH
:::
methanol HOH
:::
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
AMBER 4 LP/TIP3P c
AMBER 4 POL-LP/POL3 c
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
-3.60
-3.21
-4.59
-4.27
-6.30
-7.96
-7.65
-6.31
-7.62
-5.37
-8.66
-6.42
-6.42
-8.44
-7.63
-7.80
-8.75
-7.52
-6.14
-8.59
-6.75
-5.60
-8.11
-7.34
-5.82
-8.60
-4.77
-4.17
-5.68
-4.64
-5.53
-5.53
-5.14
-7.22
-7.22
-6.51
-5.89
-5.89
-5.32
-4.65
-4.65
-4.39
-3.79
-3.25
-3.48
-2.77
-2.77
-3.90
-5.35
-4.15
-5.06
-4.86
-3.79
-2.75
-2.35
-3.54
-4.65
-4.49
-3.70
-3.17
-0.59
-1.46
-1.65
-1.53
-1.51
-0.80
-0.32
-1.11
-1.37
-1.29
-1.30
-0.51
-5.14
-4.24
-4.24
-6.51
-6.46
-6.46
-5.32
-4.49
-4.49
-4.39
-3.55
-3.55
+0.19
+0.04
-1.11
-1.50
-3.53
-4.06
-2.30
-2.16
-2.56
-0.51
-4.87
-3.67
-4.07
-4.90
-2.98
-3.31
-5.05
-4.35
-5.55
-7.13
-5.10
-4.07
-6.60
-6.54
-5.50
-7.49
-3.40
-2.88
-4.38
-4.13
-0.39
-1.29
-0.90
-0.71
-0.76
-0.05
-0.57
-1.40
-0.83
-0.34
-1.10
-0.74
dimethyl ether HOH
:::
formaldehyde HOH
:::
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
-6.78
-6.78
-6.43
-5.69
-5.69
-5.45
-5.27
-5.27
-5.04
-7.10
-7.10
-6.61
-4.92
-4.92
-4.33
-4.12
-4.12
-3.52
-5.12
-5.12
-4.87
-4.08
-4.08
-3.83
-4.69
-4.69
-3.57
-5.73
-5.73
-4.14
-5.19
-5.19
-4.83
-4.23
-4.23
-4.01
-5.66
-5.66
-5.12
-4.61
-4.61
-4.18
-6.43
-5.26
-5.26
-5.45
-4.26
-4.26
-5.04
-3.86
-3.86
-6.61
-6.31
-6.31
-4.33
-4.05
-4.05
-3.52
-3.48
-3.48
-4.87
-4.11
-4.11
-3.83
-3.17
-3.17
-3.57
-2.23
-2.23
-4.14
-2.61
-2.61
-4.83
-4.16
-4.16
-4.01
-3.24
-3.24
-5.12
-3.69
-3.69
-4.18
-2.45
-2.45
-0.35
-1.52
-1.17
-0.24
-1.43
-1.19
-0.23
-1.41
-1.18
-0.51
-0.79
-0.30
-0.59
-0.87
-0.28
-0.60
-0.64
-0.04
-0.25
-1.01
-0.76
-0.25
-0.91
-0.66
-1.12
-2.46
-1.34
-1.59
-3.12
-1.53
-0.36
-1.03
-0.67
-0.22
-0.99
-0.77
-0.54
-1.97
-1.43
-0.43
-2.16
-1.73
furan HOH
:::
formamide formamideb
:::
formamide HOH
:::
acetamide HOH
:::
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4
AMBER POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
-3.04
-4.20
-3.00
-2.34
-4.30
-3.30
-6.16
-7.12
-6.74
-4.94
-7.26
-5.28
-6.86
-6.86
-5.23
-8.63
-8.63
-6.02
-6.99
-6.99
-6.44
-4.97
-4.97
-5.17
-8.71
-8.71
-6.98
-6.03
-6.03
-5.06
-7.02
-7.02
-5.52
-8.87
-8.87
-6.44
-7.69
-7.69
-7.27
-6.03
-6.03
-5.62
-2.09
-3.38
-3.63
-3.48
-2.87
-2.48
-2.74
-4.88
-4.70
-4.04
-4.48
-3.52
-5.23
-4.02
-4.02
-6.02
-5.09
-5.09
-6.44
-5.84
-5.84
-5.17
-5.03
-5.03
-6.98
-5.21
-5.21
-5.06
-4.00
-4.00
-5.52
-4.65
-4.65
-6.44
-6.18
-6.18
-7.27
-6.16
-6.16
-5.62
-5.52
-5.52
-0.95
-0.82
+0.63
+1.14
-1.43
-0.82
-3.42
-2.24
-2.04
-0.90
-2.78
-1.76
-1.63
-2.84
-1.21
-2.61
-3.54
-0.93
-0.55
-1.15
-0.60
+0.20
+0.06
-0.14
-1.73
-3.50
-1.77
-0.97
-2.03
-1.06
-1.50
-2.37
-0.87
-2.43
-2.69
-0.26
-0.42
-1.53
-1.11
-0.41
-0.51
-0.10
N-methyl acetamide HOH
:::
methanethiol HOH
:::
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
-8.72
-8.72
-7.66
-6.31
-6.31
-5.46
-7.26
-7.26
-5.74
-9.09
-9.09
-7.60
-7.61
-7.61
-7.26
-6.71
-6.71
-6.31
-8.91
-8.91
-7.70
-7.56
-7.56
-6.19
-2.57
-2.57
-1.46
-3.48
-3.48
-2.08
-3.76
-3.76
-2.79
-3.26
-3.26
-2.49
-4.34
-4.34
-2.99
-3.59
-3.59
-2.03
-7.66
-5.57
-5.57
-5.46
-4.45
-4.45
-5.74
-5.30
-5.30
-7.60
-6.73
-6.73
-7.26
-6.75
-6.75
-6.31
-5.94
-5.94
-7.70
-5.97
-5.97
-6.19
-4.48
-4.48
-1.46
-2.47
-2.47
-2.08
-3.39
-3.39
-2.79
-3.25
-3.25
-2.49
-2.83
-2.83
-2.99
-4.28
-4.28
-2.03
-3.61
-3.61
-1.06
-3.15
-2.09
-0.85
-1.86
-1.01
-1.52
-1.96
-0.44
-1.49
-2.36
-0.87
-0.35
-0.86
-0.51
-0.40
-0.77
-0.37
-1.21
-2.94
-1.73
-1.37
-3.08
-1.71
-1.11
-0.10
+1.01
-1.40
-0.09
+1.31
-0.97
-0.51
+0.44
-0.77
-0.43
+0.34
-1.35
-0.06
+1.29
-1.56
+0.02
+1.58
dimethyl thioether HOH
:::
methanethial HOH
:::
thiophene HOH
:::
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
I v. III
II v. III
MP2/6-31G //6-31G
I v. III
II v. III
AMBER 4/TIP3P
I v. III
II v. III
AMBER 4 POL/POL3
I v. III
II v. III
AMBER 4 LP/TIP3P
I v. III
II v. III
AMBER 4 POL-LP/POL3
I v. III
II v. III
6-31G //6-31G
MP2/6-31G //6-31G
AMBER 4/TIP3P
AMBER 4 POL/POL3
AMBER 4 LP/TIP3P
AMBER 4 POL-LP/POL3
-2.92
-2.92
-1.80
-3.97
-3.97
-2.56
-1.54
-1.54
-1.23
-1.49
-1.49
-1.15
-3.67
-3.67
-2.07
-3.13
-3.13
-1.58
-2.39
-2.39
-0.53
-3.10
-3.10
-0.78
-2.76
-2.76
-1.90
-2.40
-2.40
-1.71
-3.02
-3.02
-2.04
-2.52
-2.52
-1.74
-0.89
-1.35
-0.95
-0.76
-1.09
-0.81
-1.80
-2.85
-2.85
-2.56
-3.97
-3.97
-1.23
-1.51
-1.51
-1.15
-1.48
-1.48
-2.07
-3.66
-3.66
-1.58
-3.12
-3.12
-0.53
-0.86
-0.86
-0.78
-1.02
-1.02
-1.90
-2.43
-2.43
-1.71
-2.18
-2.18
-2.04
-2.10
-2.10
-1.74
-1.80
-1.80
-1.38
-1.83
-1.87
-1.83
-1.99
-1.80
-1.12
-0.07
+1.05
-1.41
0.00
+1.41
-0.31
-0.03
+0.28
-0.34
-0.01
+0.33
-1.60
-0.01
+1.59
-1.55
-0.01
+1.54
-1.86
-1.53
+0.33
-2.32
-2.08
+0.24
-0.86
-0.33
+0.53
-0.69
-0.22
+0.47
-0.98
-0.92
+0.06
-0.78
-0.72
+0.06
+0.49
+0.48
+0.92
+1.07
+0.90
+0.99
a
All energies in kcal
mol
b
Structure constrained to single h-bond conformation
cq
(N) = 0 to insure negative charge on lone-pair