suppmat1632. 103KB Jun 05 2011 09:30:45 PM

(1)

Supplementary Material

TABLE VII. Atomic Charges for Test Suite Molecules

Atom 6-31GRESP DFT RESP 6-31GRESP DFT RESP

C1

C2

C3

C2

C1

N H1

H2

H3

H2

H1

LP

Pyridine

N -0.547 -0.633 0.149 0.592

LP - - -0.448 -0.727

C1 0.260 0.450 0.071 -0.012

H1 0.079 0.011 0.120 0.109

C2 -0.268 -0.438 -0.235 -0.208

H2 0.141 0.160 0.147 0.133

C3 -0.021 0.190 -0.052 -0.023

H3 0.143 0.077 0.146 0.112

C3

C4 N1

C1

N2

H4

H3 H1

H2

LP

Imidazole

N1 -0.506 -0.490 0.237 0.643

LP - - -0.503 -0.739

C1 0.127 0.087 0.161 0.159

H1 0.145 0.155 -0.010 -0.149

(2)

C 3

-0.318 -0.327 -0.288 -0.254

H3 0.204 0.184 0.210 0.181

C 4

0.104 0.165 -0.065 -0.150

H4 0.118 0.081 0.153 0.155

C2

Oxazole

N -0.545 -0.513 0.114 0.403

LP 1

- - -0.423 -0.579

C1 0.438 0.400 0.172 0.179

H 1

0.077 0.052 0.051 -0.122

O -0.234 -0.178 0.458 0.686

LP 2

- - -0.439 -0.535

C 2

-0.139 -0.140 -0.327 -0.375

H 2

0.190 0.167 0.237 0.228

C 3

0.080 0.109 -0.008 -0.042

H 3

0.134 0.104 0.165 0.156

H1

Methanimine

N -0.711 -0.658 -0.090 -0.034

LP - - -0.393 -0.391

C 0.216 0.249 0.011 0.021

H 1

0.038 0.003 0.072 0.046

H 2

(3)

H3 0.382 0.350 0.273 0.241

Methyliminomethane

N -0.480 -0.486 0.214 0.667

LP - - -0.473 -0.732

C1 0.167 0.217 -0.056 -0.228

H1 0.056 0.035 0.115 0.156

H2 0.046 0.001 0.067 0.071

C2 0.074 0.193 0.009 -0.093

H 0.046 0.013 0.041 0.053

H C N LP

Hydrogen Cyanide

H 0.243 0.201 0.275 0.248

C 0.113 0.144 -0.010 -0.020

N -0.356 -0.345 -0.048 0.031

LP - - -0.216 -0.259

Ammonia

N -1.100 -0.905 0.000(-1.076)a 0.000(-1.681)a

H 0.367 0.302 0.189( 0.363)a 0.154( 0.425)a

LP - - -0.566(-0.013)a -0.461( 0.407)a

aCharge constraint removed

N

Methylamine

N -0.994 -0.912 -0.018 -0.075

(4)

C 0.309 0.292 0.225 0.232

H1 -0.018 -0.019 -0.026 -0.029

N

Dimethylamine

N -0.692 -0.639 0.140 0.699

LP - - -0.521 -0.791

H 2

0.373 0.354 0.240 0.141

C -0.010 -0.016 -0.054 -0.198

H 1

0.057 0.053 0.042 0.058

N

Trimethylamine

N -0.330 -0.202 0.279 1.103

LP - - -0.454 -0.922

C -0.109 -0.177 -0.024 -0.076

H 0.073 0.081 0.027 0.005

O

Methanol

O -0.551 -0.497 -0.099 -0.097

LP - - -0.181 -0.157

H 1

(5)

O

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

LP - - -0.191 -0.536

Formaldehyde

O -0.454 -0.394 -0.025 0.223

LP - - -0.177 -0.254

C 0.426 0.412 0.298 0.228

H 0.014 -0.009 0.040 0.029

C2

Furan

O -0.190 -0.167 0.366 0.322

LP - - -0.377 -0.331

C1 -0.007 -0.007 -0.141 -0.124

H 1

0.148 0.130 0.182 0.160

(6)

H

Formamide

O -0.567 -0.509 -0.050 -0.014

LP1 - - -0.277 -0.253

LP 2

- - -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

H 1

0.420 0.401 0.386 0.383

H 2

0.390 0.361 0.379 0.362

C1

Acetamide

O -0.610 -0.574 -0.165 -0.238

LP

-0.303 -0.444 -0.286 -0.425

H 0.089 0.121 0.091 0.120

C 2

0.813 0.810 0.688 0.715

N -1.014 -0.962 -0.984 -0.938

H 1

0.432 0.413 0.420 0.403

H 2

0.413 0.396 0.417 0.397

(7)

N

-Methyl Acetamide

O -0.570 -0.528 -0.040 0.053

LP

-0.155 -0.340 -0.148 -0.328

H1 0.046 0.089 0.052 0.093

C 2

0.627 0.615 0.493 0.476

N -0.446 -0.374 -0.434 -0.365

H 2

0.299 0.270 0.307 0.280

C3 -0.304 -0.369 -0.296 -0.362

H 3

0.137 0.152 0.133 0.148

S

Methanethiol

S -0.305 -0.269 -0.057 -0.050

LP - - -0.145 -0.128

H 1

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

S

Dimethylsulde

S -0.211 -0.185 0.028 0.024

LP - - -0.145 -0.128

C -0.238 -0.209 0.129 0.113

H 0.114 0.101 0.001 0.001

H

Methanethial

S -0.204 -0.179 0.400 0.352

(8)

S C1

C2

H2 H1

LP LP

Thiophene

S 0.014 0.013 0.325 0.286

LP - - -0.112 -0.112

C 1

-0.249 -0.219 -0.307 -0.270

H1 0.220 0.193 0.229 0.201

C 2

-0.130 -0.115 -0.129 -0.114

(9)

TABLE VIII. Total Energy of Monomer Data

a

System Model E(tot)

pyridine 6-31G//6-31G -246.69582

MP2/6-31G//6-31G -247.48038

AMBER 4 -10.05

AMBER 4/POL -59.27

AMBER 4/LP +8.48

AMBER 4/POL-LP +7.81

imidazole 6-31G//6-31G -224.81443

MP2/6-31G//6-31G -225.51613

AMBER 4 -0.33

AMBER 4/POL -1.55

AMBER 4/LP +8.46

AMBER 4/POL-LP -2.57

oxazole 6-31G//6-31G -244.63297

MP2/6-31G//6-31G -245.34580

AMBER 4 +5.31

AMBER 4/POL +3.35

AMBER 4/LP -30.78

methanimine 6-31G//6-31G -94.02846

MP2/6-31G//6-31G -94.31337

AMBER 4 +4.25

AMBER 4/POL +1.81

AMBER 4/LP -4.22

methyliminomethane 6-31G//6-31G -133.06149

MP2/6-31G//6-31G -133.47698

AMBER 4 +4.45

AMBER 4/POL +1.31

AMBER 4/LP -12.80

hydrogen cyanide 6-31G//6-31G -92.87520

MP2/6-31G//6-31G -93.15451

AMBER 4 0.00

AMBER 4/POL 0.00

AMBER 4/LP -6.27

ammonia 6-31G//6-31G -56.18436

MP2/6-31G//6-31G -56.35369

(10)

AMBER 4/POL 0.00

AMBER 4/LP 0.00

AMBER 4/POL-LP 0.00

methylamine 6-31G//6-31G -95.20983

MP2/6-31G//6-31G -95.50584

AMBER 4 -4.40

AMBER 4/POL -4.88

AMBER 4/LP +1.72

dimethylamine 6-31G//6-31G -134.23885

MP2/6-31G//6-31G -134.66444

AMBER 4 +16.96

AMBER 4/POL +14.28

AMBER 4/LP -8.61

trimethylamine 6-31G//6-31G -173.26930

MP2/6-31G//6-31G -173.82759

AMBER 4 +3.30

AMBER 4/POL -5.02

AMBER 4/LP -10.48

water 6-31G//6-31G -76.01075

MP2/6-31G//6-31G -76.19599

AMBER 4 0.00

AMBER 4/POL 0.00

AMBER 4/LP 0.00

AMBER 4/POL-LP 0.00

methanol 6-31G//6-31G -115.03542

MP2/6-31G//6-31G -115.34494

AMBER 4 +5.65

AMBER 4/POL +4.23

AMBER 4/LP -2.89

dimethyl ether 6-31G//6-31G -154.06475

MP2/6-31G//6-31G -154.50208

AMBER 4 +4.65

AMBER 4/POL +3.38

AMBER 4/LP -5.32

formaldehyde 6-31G//6-31G -113.86633

MP2/6-31G//6-31G -114.16531

(11)

AMBER 4/POL 0.00

AMBER 4/LP -3.64

furan 6-31G//6-31G -228.62521

MP2/6-31G//6-31G -229.30748

AMBER 4 +2.51

AMBER 4/POL +1.79b

AMBER 4/LP +1.20

AMBER 4/POL-LP 0.00

formamide 6-31G//6-31G -168.93070

MP2/6-31G//6-31G -169.39193

AMBER 4 -40.84

AMBER 4/POL -37.42

AMBER 4/LP +4.06

acetamide 6-31G//6-31G -207.97596

MP2/6-31G//6-31G -208.56644

AMBER 4 -91.58

AMBER 4/POL -105.11

AMBER 4/LP -33.02

N-methyl acetamide 6-31G

//6-31G -247.00601

MP2/6-31G//6-31G -247.72662

AMBER 4 +0.30

AMBER 4/POL -8.33

AMBER 4/LP +27.49

methanethiol 6-31G//6-31G -437.70032

MP2/6-31G//6-31G -437.95235

AMBER 4 +6.90

AMBER 4/POL +5.28

AMBER 4/LP -1.12

dimethyl thioether 6-31G//6-31G -476.73533

MP2/6-31G//6-31G -477.12066

AMBER 4 +0.13

AMBER 4/POL +0.10

AMBER 4/LP +4.03

methanethial 6-31G//6-31G -436.50646

MP2/6-31G//6-31G -436.75457

(12)

AMBER4/LP -5.02

AMBER4/POL-LP -3.91

thiophene 6-31G

//6-31G

-551.29035 MP2/6-31G

//6-31G

-551.92282

AMBER4 -1.08

AMBER4/POL -1.18

AMBER4/LP +22.40

AMBER4/POL-LP +24.16

a

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TABLEIX. InteractionEnergyDataa

System Model E(Form I) E(Form II) E(I II)

pyridine:::HOH 6-31G//6-31G -5.65 -2.34 -3.31

MP2/6-31G//6-31G -7.61 -3.67 -3.94

AMBER 4/TIP3P -5.25 -4.81 -0.44

AMBER 4/TIP4P -5.56 -5.04 -0.52

AMBER 4 POL/POL3 -4.93 -4.29 -0.64

AMBER 4 LP/TIP3P -7.18 -3.67 -3.51

AMBER 4 POL-LP/POL3 -7.48 -2.04 -5.44

imidazole:::HOH 6-31G//6-31G -6.53 -3.72 -2.81

MP2/6-31G//6-31G -8.37 -5.34 -3.03

AMBER 4/TIP3P -6.11 -6.33 +0.22

AMBER 4 POL/POL3 -5.40 -5.98 +0.58

AMBER 4 LP/TIP3P -8.58 -5.06 -3.52

AMBER 4 POL-LP/POL3 -8.00 -3.28 -4.72

oxazole:::HOH (N - acceptor) 6-31G//6-31G -5.23 -2.26 -2.97

MP2/6-31G//6-31G -6.74 -3.56 -3.18

AMBER 4/TIP3P -5.20 -4.35 -0.85

AMBER 4 POL/POL3 -4.42 -3.98 -0.44

AMBER 4 LP/TIP3P -6.87 -3.53 -3.34

AMBER 4 POL-LP/POL3 -7.77 -2.64 -5.13

oxazole:::HOH (O - acceptor) 6-31G//6-31G -2.24 -0.49 -1.75

MP2/6-31G//6-31G -3.29 -1.52 -1.77

AMBER 4/TIP3P -2.71 -1.42 -1.28

AMBER 4 POL/POL3 -2.08 -1.29 -0.79

AMBER 4 LP/TIP3P -3.75 -0.92 -2.83

AMBER 4 POL-LP/POL3 -3.78 -0.56 -3.22

methanimine:::HOH 6-31G//6-31G -5.65 -2.73 -2.92

MP2/6-31G//6-31G -7.10 -3.57 -3.53

AMBER 4/TIP3P -6.46 -4.98 -1.48

AMBER 4 POL/POL3 -5.99 -4.44 -1.55

AMBER 4 LP/TIP3P -7.95 -4.12 -3.83

AMBER 4 POL-LP/POL3 -7.05 -3.30 -3.75

methyliminomethane:::HOH 6-31G//6-31G -5.67 -2.41 -3.26

MP2/6-31G//6-31G -7.46 -3.65 -3.81

AMBER 4/TIP3P -5.37 -4.84 -0.53

AMBER 4 POL/POL3 -5.06 -4.35 -0.71

AMBER 4 LP/TIP3P -7.06 -3.79 -3.27

AMBER 4 POL-LP/POL3 -7.17 -2.56 -4.61

hydrogen cyanide:::HOH 6-31G//6-31G -3.62 -2.38 -1.24

(14)

AMBER 4/TIP3P -3.60 -3.79 +0.19

AMBER 4 POL/POL3 -3.21 -3.25 +0.04

AMBER 4 LP/TIP3P -4.59 -3.48 -1.11

AMBER 4 POL-LP/POL3 -4.27 -2.77 -1.50

ammonia:::HOH 6-31G//6-31G -6.30 -2.77 -3.53

MP2/6-31G//6-31G -7.96 -3.90 -4.06

AMBER 4/TIP3P -7.65 -5.35 -2.30

AMBER 4 POL/POL3 -6.31 -4.15 -2.16

AMBER 4 LP/TIP3P -7.62 -5.06 -2.56

AMBER 4 POL-LP/POL3 -5.37 -4.86 -0.51

AMBER 4 LP/TIP3Pc -8.66 -3.79 -4.87

AMBER 4 POL-LP/POL3c -6.42 -2.75 -3.67

methylamine:::HOH 6-31G//6-31G -6.42 -2.35 -4.07

MP2/6-31G//6-31G -8.44 -3.54 -4.90

AMBER 4/TIP3P -7.63 -4.65 -2.98

AMBER 4 POL/POL3 -7.80 -4.49 -3.31

AMBER 4 LP/TIP3P -8.75 -3.70 -5.05

AMBER 4 POL-LP/POL3 -7.52 -3.17 -4.35

dimethylamine:::HOH 6-31G//6-31G -6.14 -0.59 -5.55

MP2/6-31G//6-31G -8.59 -1.46 -7.13

AMBER 4/TIP3P -6.75 -1.65 -5.10

AMBER 4 POL/POL3 -5.60 -1.53 -4.07

AMBER 4 LP/TIP3P -8.11 -1.51 -6.60

AMBER 4 POL-LP/POL3 -7.34 -0.80 -6.54

trimethylamine:::HOH 6-31G//6-31G -5.82 -0.32 -5.50

MP2/6-31G//6-31G -8.60 -1.11 -7.49

AMBER 4/TIP3P -4.77 -1.37 -3.40

AMBER 4 POL/POL3 -4.17 -1.29 -2.88

AMBER 4 LP/TIP3P -5.68 -1.30 -4.38

AMBER 4 POL-LP/POL3 -4.64 -0.51 -4.13

methanol:::HOH 6-31G//6-31G -5.53 -5.14 -0.39

AMBER 4/TIP3P -5.89 -5.32 -0.57

I v. III -5.89 -4.49 -1.40

II v. III -5.32 -4.49 -0.83

AMBER 4 POL/POL3 -4.65 -4.39 -0.34

I v. III -4.65 -3.55 -1.10

(15)

AMBER 4 LP/TIP3P -6.78 -6.43 -0.35

I v. III -6.78 -5.26 -1.52

II v. III -6.43 -5.26 -1.17

AMBER 4 POL-LP/POL3 -5.69 -5.45 -0.24

I v. III -5.69 -4.26 -1.43

II v. III -5.45 -4.26 -1.19

dimethyl ether:::HOH 6-31G//6-31G -5.27 -5.04 -0.23

I v. III -5.27 -3.86 -1.41

II v. III -5.04 -3.86 -1.18

MP2/6-31G//6-31G -7.10 -6.61 -0.51

I v. III -7.10 -6.31 -0.79

II v. III -6.61 -6.31 -0.30

AMBER 4/TIP3P -4.92 -4.33 -0.59

I v. III -4.92 -4.05 -0.87

II v. III -4.33 -4.05 -0.28

AMBER 4 POL/POL3 -4.12 -3.52 -0.60

I v. III -4.12 -3.48 -0.64

II v. III -3.52 -3.48 -0.04

AMBER 4 LP/TIP3P -5.12 -4.87 -0.25

I v. III -5.12 -4.11 -1.01

II v. III -4.87 -4.11 -0.76

AMBER 4 POL-LP/POL3 -4.08 -3.83 -0.25

I v. III -4.08 -3.17 -0.91

II v. III -3.83 -3.17 -0.66

formaldehyde:::HOH 6-31G//6-31G -4.69 -3.57 -1.12

I v. III -4.69 -2.23 -2.46

II v. III -3.57 -2.23 -1.34

MP2/6-31G//6-31G -5.73 -4.14 -1.59

I v. III -5.73 -2.61 -3.12

II v. III -4.14 -2.61 -1.53

AMBER 4/TIP3P -5.19 -4.83 -0.36

I v. III -5.19 -4.16 -1.03

II v. III -4.83 -4.16 -0.67

AMBER 4 POL/POL3 -4.23 -4.01 -0.22

I v. III -4.23 -3.24 -0.99

II v. III -4.01 -3.24 -0.77

AMBER 4 LP/TIP3P -5.66 -5.12 -0.54

I v. III -5.66 -3.69 -1.97

II v. III -5.12 -3.69 -1.43

AMBER 4 POL-LP/POL3 -4.61 -4.18 -0.43

I v. III -4.61 -2.45 -2.16

(16)

furan:::HOH 6-31G//6-31G -3.04 -2.09 -0.95

MP2/6-31G//6-31G -4.20 -3.38 -0.82

AMBER 4/TIP3P -3.00 -3.63 +0.63

AMBER 4 POL/POL3 -2.34 -3.48 +1.14

AMBER 4 LP/TIP3P -4.30 -2.87 -1.43

AMBER 4 POL-LP/POL3 -3.30 -2.48 -0.82

formamide:::formamideb 6-31G//6-31G -6.16 -2.74 -3.42

MP2/6-31G//6-31G -7.12 -4.88 -2.24

AMBER 4 -6.74 -4.70 -2.04

AMBER POL3 -4.94 -4.04 -0.90

AMBER 4 LP/TIP3P -7.26 -4.48 -2.78

AMBER 4 POL-LP/POL3 -5.28 -3.52 -1.76

formamide:::HOH 6-31G//6-31G -6.86 -5.23 -1.63

AMBER 4/TIP3P -6.99 -6.44 -0.55

I v. III -6.99 -5.84 -1.15

II v. III -6.44 -5.84 -0.60

AMBER 4 POL/POL3 -4.97 -5.17 +0.20

I v. III -4.97 -5.03 +0.06

II v. III -5.17 -5.03 -0.14

AMBER 4 LP/TIP3P -8.71 -6.98 -1.73

I v. III -8.71 -5.21 -3.50

II v. III -6.98 -5.21 -1.77

AMBER 4 POL-LP/POL3 -6.03 -5.06 -0.97

I v. III -6.03 -4.00 -2.03

AMBER 4/TIP3P -7.69 -7.27 -0.42

I v. III -7.69 -6.16 -1.53

II v. III -7.27 -6.16 -1.11

AMBER 4 POL/POL3 -6.03 -5.62 -0.41

I v. III -6.03 -5.52 -0.51

(17)

AMBER 4 LP/TIP3P -8.72 -7.66 -1.06

I v. III -8.72 -5.57 -3.15

II v. III -7.66 -5.57 -2.09

AMBER 4 POL-LP/POL3 -6.31 -5.46 -0.85

I v. III -6.31 -4.45 -1.86

II v. III -5.46 -4.45 -1.01

N-methyl acetamide

:::HOH 6-31G//6-31G -7.26 -5.74 -1.52

AMBER 4/TIP3P -7.61 -7.26 -0.35

I v. III -7.61 -6.75 -0.86

II v. III -7.26 -6.75 -0.51

AMBER 4 POL/POL3 -6.71 -6.31 -0.40

I v. III -6.71 -5.94 -0.77

II v. III -6.31 -5.94 -0.37

AMBER 4 LP/TIP3P -8.91 -7.70 -1.21

I v. III -8.91 -5.97 -2.94

II v. III -7.70 -5.97 -1.73

AMBER 4 POL-LP/POL3 -7.56 -6.19 -1.37

I v. III -7.56 -4.48 -3.08

II v. III -6.19 -4.48 -1.71

methanethiol:::HOH 6-31G//6-31G -2.57 -1.46 -1.11

I v. III -2.57 -2.47 -0.10

II v. III -1.46 -2.47 +1.01

MP2/6-31G//6-31G -3.48 -2.08 -1.40

I v. III -3.48 -3.39 -0.09

II v. III -2.08 -3.39 +1.31

AMBER 4/TIP3P -3.76 -2.79 -0.97

I v. III -3.76 -3.25 -0.51

II v. III -2.79 -3.25 +0.44

AMBER 4 POL/POL3 -3.26 -2.49 -0.77

I v. III -3.26 -2.83 -0.43

II v. III -2.49 -2.83 +0.34

AMBER 4 LP/TIP3P -4.34 -2.99 -1.35

I v. III -4.34 -4.28 -0.06

II v. III -2.99 -4.28 +1.29

AMBER 4 POL-LP/POL3 -3.59 -2.03 -1.56

I v. III -3.59 -3.61 +0.02

(18)

dimethyl thioether:::HOH 6-31G//6-31G -2.92 -1.80 -1.12

AMBER 4/TIP3P -1.54 -1.23 -0.31

I v. III -1.54 -1.51 -0.03

II v. III -1.23 -1.51 +0.28

AMBER 4 POL/POL3 -1.49 -1.15 -0.34

I v. III -1.49 -1.48 -0.01

II v. III -1.15 -1.48 +0.33

AMBER 4 LP/TIP3P -3.67 -2.07 -1.60

I v. III -3.67 -3.66 -0.01

II v. III -2.07 -3.66 +1.59

AMBER 4 POL-LP/POL3 -3.13 -1.58 -1.55

I v. III -3.13 -3.12 -0.01

II v. III -1.58 -3.12 +1.54

methanethial:::HOH 6-31G//6-31G -2.39 -0.53 -1.86

I v. III -2.39 -0.86 -1.53

II v. III -0.53 -0.86 +0.33

MP2/6-31G//6-31G -3.10 -0.78 -2.32

I v. III -3.10 -1.02 -2.08

II v. III -0.78 -1.02 +0.24

AMBER 4/TIP3P -2.76 -1.90 -0.86

I v. III -2.76 -2.43 -0.33

II v. III -1.90 -2.43 +0.53

AMBER 4 POL/POL3 -2.40 -1.71 -0.69

I v. III -2.40 -2.18 -0.22

II v. III -1.71 -2.18 +0.47

AMBER 4 LP/TIP3P -3.02 -2.04 -0.98

I v. III -3.02 -2.10 -0.92

II v. III -2.04 -2.10 +0.06

AMBER 4 POL-LP/POL3 -2.52 -1.74 -0.78

I v. III -2.52 -1.80 -0.72

II v. III -1.74 -1.80 +0.06

thiophene:::HOH 6-31G//6-31G -0.89 -1.38 +0.49

MP2/6-31G//6-31G -1.35 -1.83 +0.48

AMBER 4/TIP3P -0.95 -1.87 +0.92

AMBER 4 POL/POL3 -0.76 -1.83 +1.07

AMBER 4 LP/TIP3P -1.09 -1.99 +0.90

(19)

a

All energies in

kcal

mol

b

Structure constrained to single h-bond conformation

c