SMTables.doc 389KB Jun 05 2011 09:30:49 PM

MMFF VII. Characterization of MMFF94, MMFF94s, and Other Widely Available

Force Fields for Conformational Energies and for Intermolecular-Interaction

Energies and Geometries.

THOMAS A. HALGREN

Molecular Systems, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065

Contents:

Comparisons of ab initio "MP4SDQ/TZP" and calculated force-field results for 147 conformational energies:

• Table SM-I

Detailed comparisons of calculated force-field intermolecular interaction energies and geometries to scaled quantum mechanical results:

• MMFF94 (Table SM-II)

• MMFF94s (Table SM-III)

• CFF95 (Table SM-IV)

• CVFF (Table SM-V)

Conformational comparison

"MP4/ TZP" MMFF 94s MMFF 94 CFF 95 MSI CHARMm AMBER*

OPLS* MM2* MM3*

Amides:

N

-methylformamide, cis - trans

1.03

1.09

1.28

1.83

3.44#

1.57

0.41

0.46

1.50

N

-methylactamide, cis - trans

1.90

1.97

2.18

3.09

2.46

2.33

1.98

1.74

2.31

N

-formylformamide,

o=c-n-h cis,trans - cis,cis

0.41

0.44

0.40

0.95

2.68#

0.37

-0.98

-1.10#

1.72

glycine dipeptide analog, C5 - C7

0.91

1.08

1.14

-0.16

2.13

1.29

0.37

5.24##

0.65

alanine dipeptide analog, C5 - C7eq

1.08

1.11

1.12

0.76

2.58#

1.68

1.69

5.52##

0.00

alanine dipeptide analog, C7ax - C7eq

2.20

1.58

1.83

1.43

1.43

1.72

2.98

1.36

1.16

alanine dipeptide analog,



'- C7eq

4.88

5.24

4.85

4.54

7.04#

6.22

4.32

---

3.60

alanine dipeptide analog,



₂

' - C7eq

2.76

---

2.47

---

---

---

1.84

---

---alanine dipeptide analog,



_L

- C7eq

4.10

4.28

3.87

---

---

---

---

---

1.16#

N

-OH,

N

-methylacetamide,

o-n-c=o cis - trans

0.04

-0.19

0.01

1.95#

-5.40## -5.03## -9.38## ---

---N

-OH,

N

-Et acetamide,

[o-n-c=o trans, c-c-n-o g] -

[o-n-c=o cis, c-c-n-c(=o) g]

0.24

0.53

0.14

-1.97#

2.55#

4.81## 10.08## ---

---N

-OH,

N

-Et acetamide,

[o-n-c=o trans, c-c-n-o trans] -

[o-n-c=o cis, c-c-n-c(=o) g]

1.50

---

1.56

-2.39## ---

---

9.32## ---

---N

-OH,

N

-Et acetamide,

[image:3.792.78.703.135.544.2]

[o-n-c=o cis, c-c-n-c(=o) g]

N

-OH,

N

-Me propionamide,

[o-n-c=o trans, c-c-c=o cis] -

[o-n-c=o cis, c-c-c=o cis]

---N

-OH,

N

-Me propionamide,

[o-n-c=o trans, c-c-c=o sk] -

[o-n-c=o cis, c-c-c=o cis]

0.96

1.24

1.07

-2.41##

3.42#

5.17## 11.29## ---

---N

-OH,

N

-Me propionamide,

[o-n-c=o cis, c-c-c=o sk] -

[o-n-c=o cis, c-c-c=o cis]

0.72

1.24

1.09

0.26

0.26

---

2.19

---

---glycine dipeptide, C5 - C7

1.66

1.40

1.62

1.08

2.55

-1.20#

-0.70#

5.65##

1.25

alanine dipeptide, C5 - C7eq

1.64

1.42

1.68

1.79

2.93

-0.69#

0.44

6.05##

0.56

alanine dipeptide, C7ax - C7eq

2.20

1.84

2.26

1.17

1.84

2.19

2.95

1.53

1.34

alanine dipeptide,



' - C7eq

5.35

5.66

5.47

5.34

7.30# ---

5.48

---

4.26

alanine dipeptide,



₂

- C7eq

3.20

---

3.06

---

---

---

---

---

---alanine dipeptide,



_L

- C7eq

4.25

4.74

4.75

---

---

---

---

---

---Carboxylic Acids:

formic acid, trans - cis

4.79

4.89

4.89

4.48

5.97

6.55#

7.64# 11.38##

4.89

acetic acid, trans - cis

5.86

5.87

5.87

6.05

4.76

7.23

6.67

13.66##

5.70

propanoic acid, c-c-c=o sk - cis

0.85

0.84

0.84

0.90

0.80

-0.22

-0.10

0.52

0.71

gyloxylic acid,

[o=c-c=o trans, o=c-o-h cis] -

[o=c-c=o trans, o=c-o-h trans]

0.35

1.91#

1.91#

2.94#

0.89

1.07

5.08## -5.68## -0.49

glycolic acid, o=c-c-o sk - cis

1.64

0.80

0.80

2.57

-2.76## -0.71#

-3.50##

0.94

2.88

propenoic acid, c=c-c=o trans - cis

0.21

0.25

0.25

0.70

-0.39

-0.03

-0.14

-0.05

-1.17

oxalic acid,

[o=c-c=o trans, o=c-o-h trans,trans]

oxalic acid,

[o=c-c=o trans, o=c-o-h cis,trans] -

[o=c-c=o trans, o=c-o-h trans,trans]

pyruvic acid,

[o=c-c=o cis, o=c-o-h cis] -

[o=c-c=o trans, o=c-o-h trans]

1.67

2.42

2.42

2.97

2.48

1.52

4.42#

-4.13## -0.16#

Esters:

methyl formate, o=c-o-c trans - cis

5.65

5.28

5.28

5.09

5.54

1.34##

0.87##

5.61

2.18##

methyl acetate, o=c-o-c trans - cis

8.21

8.27

8.27

8.67

9.09

7.42

7.47

6.68#

7.85

vinyl formate, c=c-o-c cis - trans

2.79

2.83

2.83

---

4.79# ---

---

2.84

---ethyl formate, c-o-c-c g - a

0.34

0.44

0.44

0.67

---

0.99

0.69

0.27

0.23

isopropyl formate, c-c-o-c g,g - g,a

2.43

2.43

2.43

2.16

5.58##

2.65

2.84

0.74#

1.60

phenyl acetate, o=c-o-c cis - trans

4.30

4.50

4.50

2.58#

1.32#

2.06#

4.93

8.80##

1.28##

methyl glycolate, o=c-c-o sk - cis

1.48

2.43

2.43

2.40

-3.25##

0.35

-0.03#

2.22

2.84

Congujated systems:

1,3-butadiene, g - s-trans

2.39

2.46

2.46

3.39

2.39

2.45

2.80

2.74

1.72

2-methyl-1,3-butadiene, g - s-trans

2.20

2.12

2.12

2.79

1.95

3.29

1.85

2.49

1.63

2-methyl-but-1-ene-3-one,

2-methylpropenoic acid,

c=c-c=o cis - trans

0.60

0.62

0.62

-0.45

0.71

-0.52

0.38

-1.18#

1.30

1,3-pentadiene,

[c=c-c=c g, c-c=c-c trans] -

[c=c-c=c s-trans, c-c=c-c trans]

1,3-pentadiene,

[s-trans, c-c=c-c cis] -

[s-trans, c-c=c-c trans]

1.27

2.11

2.11

2.15

0.70

1.29

1.97

2.23

1.12

Aldehydes and ketones:

propionaldehyde, c-c-c=o sk - cis

0.83

0.53

0.53

1.09

0.32

1.65

-0.46

0.90

1.10

2-butanone c-c-c=o sk - cis

0.98

0.83

0.83

1.35

0.19

1.73

-0.04

1.57

1.61

methyl ispropyl ketone,

o=c-c(ch3)2-h cis - trans

0.69

0.89

0.89

1.24

0.87

1.65

0.40

1.36

1.53

butyraldehyde, c-c-c-c g - a

0.14

0.11

0.11

0.87

0.89

1.27

1.08

0.84

0.91

but-3-enal,

[c=c-c-c sk, c-c-c=o cis] -

[c=c-c-c sk+, c-c-c=o sk+]

0.20

-0.05

-0.05

---

1.16

-0.96

-0.11

0.95

2.11#

but-3-enal,

[c=c-c-c sk-, c-c-c=o sk+] -

[c=c-c-c sk+, c-c-c=o sk+]

0.29

0.98

0.98

0.65

0.71

0.51

0.62

0.07

0.51

3-methyl-but-3-enal,

[c=c-c-c sk, c-c-c=o cis] -

[c=c-c-c sk, c-c-c=o sk]

0.43

0.72

0.72

0.06

1.34

0.08

1.31

1.25

2.68#

isobutyraldehyde, h-c(=0)-c-h a - g

0.37

0.56

0.56

0.97

0.04

1.58

-0.49

0.99

1.16

2-formylpropanal, o-c-c-c(=o) a - g

0.18

0.14

0.14

0.01

-3.85## -2.60#

-1.94#

0.25

-0.33

4-oxobutanal (o=c-c-c, c-c-c=o cis, cis),

Halides:

1-chloropropane, g - a

0.03

0.00

0.00

1.03

0.15

0.07

0.39

0.23

0.29

Imines, guanidines, and amidines

formamidine (

N

puckered),

h-n=c-n cis - trans

2.03

2.03

2.27

1.62

2.08

1.78

4.23#

-0.96#

-0.68#

N

-methylformamidine (

N

puckered),

n-c=n-c cis - trans

2.00

2.00

2.12

2.67

-3.12##

3.82# ---

-0.09#

1.03

butadiene schiff base,

[c=c-c=n s-cis, h-n=c-c trans] -

[c=c-c=n s-trans, h-n=c-c cis]

1.73

1.94

1.94

6.58##

2.63

1.96

1.89

2.60

1.99

Ketals, acetals, and hemiacetals:

2-methoxytetrahydropyran,

[eq, me-o-c-c a] - [ax, me-o-c-c a]

1.30

1.81

1.81

1.88

2.37

0.97

1.70

2.27

1.63

2,4-dioxapentane,

[c-o-c-o g, o-c-o-c a] -

[c-o-c-o g+, o-c-o-c g+]

2.44

2.11

2.11

2.54

3.37

2.95

1.93

2.99

2.26

2,5-dimethyl-1,3-dioxane, 5-ax - 5-eq

0.63

0.50

0.50

0.04

-0.65

-0.67

0.41

0.69

0.75

methoxymethanol,

[c-o-c-o g+, o-c-o-h g-] -

[c-o-c-o g+, o-c-o-h g+]

2.25

2.97

2.97

1.96

-3.98##

2.34

2.86

2.84

2.94

Cations:

---Amines:

isopropylamine,

[

C

₁

, h-c-n-lp g] -

[

C

_s

, h-c-n-lp a]

0.50

0.45

0.45

0.16

-0.07

0.23

0.00

0.15

0.22

cyclohexylamine, ax - eq

0.69

0.67

0.67

0.83

1.78

-0.74

0.62

1.38

1.23

piperidine, n-h ax - eq

0.78

0.90

0.90

0.05

0.13

0.14

-0.04

0.31

0.31

N

-methylpiperidine, ax - eq

3.58

3.28

3.28

3.25

2.70

1.26#

2.32

2.53

2.31

ethylamine, c-c-n-lp a - g

0.08

0.44

0.44

0.20

0.22

0.26

0.00

0.14

0.12

3-aminopropene,

[c=c-c-n cis, c-c-n-lp g] -

[c=c-c-n sk, c-c-n-lp g]

0.50

0.51

0.51

2.44#

0.00

-0.84

-1.07#

0.71

1.82

3-aminopropene,

[c=c-c-n sk, c-c-n-lp a] -

[c=c-c-n sk, c-c-n-lp g]

0.15

0.65

0.65

-0.17

-0.21

-0.18

0.68

-0.30

-0.08

2-methyl,3-aminopropene,

[c=c-c-n cis, c-c-n-lp g] -

[c=c-c-n sk, c-c-n-lp g]

0.67

0.61

0.61

1.19

0.47

0.32

-0.93#

1.03

1.75

ethylenediamine,

[n-c-c-n a, c-c-n-lp g+, g+] -

[n-c-c-n g+, c-c-n-lp g+, g+]

1.39

1.45

1.45

0.84

1.48

12.94## 21.84##

1.20

0.59

---Alcohols:

ethanol, a - g

0.06

-0.18

-0.18

-0.37

-0.23

-0.36

0.00

-0.60

-0.41

n

-propanol,

[c-c-c-o g-, c-c-o-h g+] -

[c-c-c-o a, c-c-o-h g]

n

-propanol,

[c-c-c-o g+, c-c-o-h g+] -

[c-c-c-o a, c-c-o-h g]

0.05

0.24

0.24

0.01

-0.43

-0.62

0.28

0.36

0.35

n

-propanol,

[c-c-c-o a, c-c-o-h a] -

[c-c-c-o a, c-c-o-h g]

0.20

-0.17

-0.17

-0.49

-0.16

-0.30

0.00

-0.60

-0.42

n

-propanol,

[c-c-c-o g, c-c-o-h a] -

[c-c-c-o a, c-c-o-h g]

0.10

0.12

0.12

-0.23

-0.29

-0.81

0.28

-0.30

-0.06

isopropanol, h-c-o-h a - g

0.20

0.17

0.17

0.40

0.02

0.25

0.00

0.61

0.68

cyclopentanol, eq

C

_s

- ax

C

₁

1.11

0.82

0.82

-0.27

---

-0.36

-0.07

0.40

0.89

cyclopentanol, ax

C

_s

- ax

C

₁

1.05

0.59

0.59

-0.33

-0.94# ---

0.00

0.82

1.35

cyclopentanol, eq

C

₁

- ax

C

₁

1.14

0.47

0.47

-0.53#

-0.62#

0.70

-0.07

-0.23

-0.15

cyclohexanol, eq

C

_s

- eq

C

₁

0.18

0.20

0.20

0.38

0.06

0.15

0.00

0.62

0.77

cyclohexanol, ax

C

_s

- eq

C

₁

1.14

1.01

1.01

-0.49#

0.58

-0.87#

0.50

1.46

2.43

cylohexanol, ax

C

₁

- eq

C

₁

0.33

0.32

0.32

0.24

0.40

-0.57

0.50

0.58

0.74

vinyl alcohol, c=c-o-h trans - sk

1.43

1.43

1.43

1.58

0.66

-0.81#

-0.69#

1.75

-0.09#

benzyl alcohol, h-o-c-c a - g

1.13

1.59

1.59

1.38

2.97#

0.81

1.23

1.22

1.33

propen-3-ol,

[c=c-c-o sk, c-c-o-h a] -

[c=c-c-o sk, c-c-o-h g]

1.24

1.10

1.10

0.82

2.43

1.07

0.19

1.20

1.12

propen-3-ol,

[c=c-c-o cis, c-c-o-h a] -

[c=c-c-o sk, c-c-o-h g]

2-me-propen-3-ol,

[c=c-c-o c, c-c-o-h a] -

[c=c-c-o s, c-c-o-h a]

0.38

0.47

0.47

0.94

0.39

-0.71

-1.57#

-0.10

1.53

sec-butanol, ag/ag - ga/ag

0.48

0.47

0.47

0.57

1.02

0.93

0.71

0.53

0.49

sec-butanol, ag/ga - ga/ag

0.29

0.46

0.46

0.74

1.06

0.85

0.71

0.53

0.50

sec-butanol, ag/gg - ga/ag

0.56

0.59

0.59

1.15

0.87

1.07

0.71

1.14

1.14

sec-butanol, gg/ag - ga/ag

0.75

0.72

0.72

0.87

0.79

0.40

1.00

0.82

0.98

sec-butanol, gg/ga - ga/ag

0.57

0.66

0.66

0.68

0.43

0.20

1.00

0.90

0.97

sec-butaone, gg/gg - ga/ag

1.13

1.14

1.14

0.56

1.01

0.33

1.00

1.54

2.06

1,2-ethanediol,

[h-o-c-c a, o-c-c-o a, c-c-o-h a] -

[h-o-c-c g-, o-c-c-o g+, c-c-o-h a]

2.71

2.91

2.91

0.70#

2.45

5.69# 17.30##

2.30

0.80#

1,2-ethanediol,

[h-o-c-c g-, o-c-c-o g+, c-c-o-h g+] -

[h-o-c-c g-, o-c-c-o g+, c-c-o-h a]

0.49

1.15

1.15

1.45

0.79

0.29

---

1.47

---1,2-ethanediol,

[h-o-c-c g+, o-c-c-o g-, c-c-o-h g+] -

[h-o-c-c g-, o-c-c-o g+, c-c-o-h a]

1.41

1.58

1.58

1.92

1.17

0.37

---

1.50

---Ethers:

methyl ethyl ether, g - a

1.41

1.50

1.50

1.46

1.53

1.79

1.85

1.74

1.48

methyl vinyl ether, c=c-o-c skew - cis

2.27

2.22

2.22

-3.10##

2.10

-2.90## -3.94##

1.07

0.60#

diethyl ether,

[ccoc a, cocc g]

[c-c-o-c a, c-o-c-c a]

1.48

1.52

1.52

1.37

1.55

1.83

1.84

1.77

1.49

methyl isopropyl ether, h-c-o-ch3 a - g

1.91

1.88

1.88

2.10

1.91

2.25

2.20

1.73

2.12

Alkanes:

cyclohexane, twist-boat - chair

6.14

5.93

5.93

7.08

6.72

5.79

6.77

5.36

5.76

methylcyclohexane, ax - eq

1.69

1.37

1.37

1.84

1.80

0.90

1.78

1.78

1.77

2,3-dimethylbutane, h-c2-c3-h g - a

0.04

-0.23

-0.23

0.13

0.40

-0.22

-0.48

0.15

0.38

cyclooctane, D4d crown - Cs boat-chair

2.00

1.44

1.44

1.21

0.45#

0.83

-1.67##

0.96

1.12

cyclooctane,

C

₂

twist-boat-chair -

C

_s

boat-chair

1.71

1.99

1.99

2.30

1.88

1.77

1.20

1.66

1.85

cyclooctane,

S

₄

-

C

_s

boat-chair

2.97

3.27

3.27

0.16#

4.48#

3.63

6.51##

3.12

2.62

methylcyclobutane, ax - eq

0.77

0.78

0.78

1.21

0.06

0.17

0.63

0.58

0.92

cyclononane,

C

₂

[144] -

D

₃

[333]

1.97

1.41

1.41

1.02

0.37#

0.53

-1.02#

0.77

1.15

cyclononane,

C

₂

[225] -

D

₃

[333]

0.99

1.21

1.21

-1.63#

1.12

1.07

0.80

0.75

0.84

cyclononane,

C

₁

[234] -

D

₃

[333]

3.65

3.81

3.81

2.03#

3.45

3.66

4.31

3.16

3.04

Alkenes:

1-butene, c=c-c-c cis - sk

0.26

0.26

0.26

0.72

0.46

0.66

1.00

0.49

0.68

1-pentene (c=c-c-c skew),

c-c-c-c g - a

0.61

0.51

0.51

0.90

-0.10

0.11

0.60

0.78

0.42

2-methyl-1-butene, c=c-c-c skew - cis

0.02

-0.03

-0.03

-0.07

-0.93

-0.97

-0.98

-0.06

-0.38

1,4-pentadiene,

c=c-c-c sk+,sk- - sk-,sk-

0.33

0.43

0.43

0.33

0.19

0.44

0.25

0.07

0.27

2-butene, cis - trans

1.27

1.35

1.35

1.43

1.61

1.55

2.49

1.43

1.02

2-pentene,

[c-c=c-c cis, c-c-c=c sk] -

[c-c=c-c trans, c-c-c=c sk]

Thiols, sulfides, and disulfides:

1-propanethiol,

[s-c-c-c g-, h-s-c-c g+] -

[s-c-c-c a, h-s-c-c g]

0.30

0.37

0.37

1.59

-0.84

1.51

0.48

0.84

1.04

1-propanethiol,

[s-c-c-c g, h-s-c-c a] -

[s-c-c-c a, h-s-c-c g]

1.23

0.95

0.95

2.26

-1.65#

1.53

0.48

0.92

0.65

1,2-ethanedithiol,

[all anti] -

[h-s-c-c a,g+, s-c-c-s g-]

0.86

1.17

1.17

0.15

-0.95#

6.92##

5.17#

-0.92#

-1.71#

1,2-ethanedithiol,

[h-s-c-c a,a, s-c-c-s g] -

[h-s-c-c a,g+, s-c-c-s g-]

1.77

2.24

2.24

1.71

0.26#

1.62

5.51##

0.68

0.34

methyl propyl sulfide,

[c-s-c-c g-, s-c-c-c g-] -

[c-s-c-c g, s-c-c-c a]

0.09

0.05

0.05

1.56

-0.08

1.21

0.12

0.58

0.61

methyl propyl sulfide,

[c-s-c-c a, s-c-c-c g] -

[c-s-c-c g, s-c-c-c a]

0.66

0.60

0.60

-0.03

0.18

0.94

-0.24

0.24

0.51

methyl propyl sulfide,

[c-s-c-c a, s-c-c-c a] -

[c-s-c-c g, s-c-c-c a]

0.25

0.33

0.33

-1.66#

0.23

-0.24

-0.43

-0.39

-0.18

a

For the OH14 conformers (sec-butanol), in the conformational designations "wx/yz", "w" indicates the conformation of the c-c-c-o

angle, "x" that of the c-c-c-c angle,"y" that of the h-o-c-ch

2

angle, and "z" that of the h-o-c-ch

3

angle.

[image:22.792.67.732.122.532.2]

TABLE SM-II.

_________________________________________________________________________________

MMFF94 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.61 -0.14 2.73 2.75 0.02 2.03 1.78 172.3 170.4

HOH...HOH, cyclic C_s (2) -5.02 -4.91 0.11 2.58 2.78 0.19 2.31 2.19 111.8 117.0

2.58 2.78 0.19 2.31 2.19 111.8 117.0

HOH...OHCH₃ (3) -6.10 -6.33 -0.23 2.72 2.73 0.02 2.01 1.76 169.0 168.7

CH3OH...OH2 (4) -6.15 -6.15 0.00 2.72 2.75 0.03 2.01 1.76 174.9 179.9

CH₃OH...OHCH₃ (5) -6.09 -6.04 0.05 2.71 2.73 0.02 2.00 1.74 174.6 177.0

HOH...O(CH₃)₂ (6) -5.84 -5.98 -0.14 2.71 2.77 0.06 2.02 1.81 163.9 166.7

C6H5OH...OH2 (7) -8.10 -8.45 -0.35 2.67 2.69 0.02 1.95 1.72 174.0 167.5

HOH...OHC₆H₅ (8) -5.18 -5.08 0.10 2.79 2.83 0.04 2.12 1.89 160.8 159.9

t-Vinyl alcohol...OH₂ (9) -8.18 -8.48 -0.30 2.65 2.68 0.02 1.93 1.69 175.0 176.1 HOH...t-Vinyl alcohol (10) -5.16 -5.46 -0.30 2.79 2.81 0.02 2.11 1.87 163.2 160.4

HOH...Furan (11) -4.00 -3.78 0.22 2.78 2.88 0.10 2.22 1.97 141.6 155.4

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -17.09 0.01 2.57 2.62 0.05 1.83 1.63 175.9 169.2

2.57 2.62 0.05 1.83 1.63 175.9 169.2

H3CCOOH...OHH (13) -10.94 -11.70 -0.76 2.58 2.64 0.07 1.90 1.67 156.3 163.4

2.61 2.77 0.16 2.15 2.11 127.9 122.8

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -12.72 -1.49 2.54 2.61 0.07 1.80 1.61 171.5 175.4

2.61 2.60 -0.02 2.22 1.92 122.2 123.9

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -6.10 -1.20 2.97 2.94 -0.04 2.44 2.02 141.1 155.7

HOH...skew-Methyl vinyl ether (17) -5.20 -4.80 0.40 2.73 2.87 0.14 2.08 1.94 155.6 159.0 HOH...Methyl formate (=O) (18) -6.39 -6.84 -0.45 2.76 2.73 -0.03 2.06 1.75 167.0 177.6 HOH...Methyl formate (-O-) (19) -3.82 -2.62 1.20 2.78 2.95 0.17 2.24 2.12 138.7 142.0

HOH...Formaldehyde (20) -5.81 -6.74 -0.93 2.72 2.71 0.00 2.11 1.74 147.6 170.5

HOH...Acetone (21) -6.87 -7.06 -0.19 2.74 2.71 -0.03 2.06 1.73 163.1 173.1

t-NMA...OH₂ (22) -5.97 -6.86 -0.89 2.87 2.84 -0.03 2.12 1.82 178.3 176.9

HOH...t-NMA (23) -8.03 -8.19 -0.16 2.70 2.71 0.00 2.00 1.73 167.6 174.2

Formamide dimer, cyclic (24) -14.78 -12.26 2.52 2.76 2.81 0.06 2.00 1.79 171.6 173.4

2.76 2.81 0.06 2.00 1.79 171.5 173.4

Formamide dimer, parallel (25) -8.12 -7.69 0.43 2.80 2.76 -0.03 2.09 1.74 156.7 174.4

t-NMA dimer, antiparallel (26) -7.70 -9.08 -1.38 2.83 2.76 -0.07 2.08 1.76 171.8 165.3

t-NMA antiparallel stacked (27) -3.86 -5.62 -1.76 3.65 3.61 -0.05 3.88 3.49 87.9 88.5

3.67 3.61 -0.06 3.88 3.49 88.9 88.4

HOH...N-Methylformamide (28) -7.90 -8.07 -0.17 2.71 2.71 0.00 2.01 1.73 164.7 174.8 N-Methylformamide...OH2 (29) -6.05 -6.94 -0.89 2.84 2.82 -0.01 2.09 1.80 173.8 175.4

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -7.99 0.22 2.62 2.70 0.08 1.94 1.72 159.2 175.8 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -3.95 0.15 2.82 2.85 0.03 2.12 1.87 168.7 175.8 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -3.02 0.49 3.01 3.11 0.10 2.60 2.40 123.9 125.4

3.01 3.11 0.10 2.61 2.40 123.8 125.4

H₂NH...NH₃, linear C_s (33) -3.38 -3.67 -0.29 3.15 3.03 -0.12 2.42 2.00 179.0 178.1

3.15 3.03 -0.12 3.64 3.36 69.8 62.7

HOH...NH3 (34) -7.22 -6.83 0.39 2.80 2.80 0.00 2.09 1.82 176.4 173.9

Imidazole...OH₂ (36) -7.00 -7.91 -0.91 2.79 2.82 0.04 2.03 1.81 178.2 175.6

HOH...Imidazole (37) -7.77 -7.93 -0.16 2.73 2.75 0.01 2.10 1.81 151.2 158.6

Indole...OH₂ (38) -6.33 -6.51 -0.18 2.81 2.86 0.05 2.07 1.84 168.3 179.7

Pyrrole...OH2 (39) -5.89 -6.28 -0.39 2.82 2.86 0.04 2.07 1.84 180.0 180.0

HOH...Pyridine (40) -6.63 -7.10 -0.47 2.77 2.79 0.02 2.12 1.85 155.8 158.9

Formamidine...H2O, cyclic (41) -11.03 -10.65 0.38 2.81 2.97 0.15 2.20 2.09 143.3 142.8

2.70 2.76 0.06 2.06 1.80 151.4 162.0

HOH...Formaldehydeimine (42) -6.74 -7.95 -1.21 2.76 2.74 -0.02 2.11 1.77 154.0 167.6

Guanidine...OHH (43) -7.96 -7.47 0.49 2.88 2.90 0.02 2.25 1.98 145.4 148.1

2.77 2.94 0.18 2.21 2.11 141.1 141.1

Vinylamine...OH2 (44) -3.80 -4.61 -0.81 3.04 2.87 -0.17 2.19 1.85 164.2 173.3

Aniline...OH₂ (45) -4.62 -4.86 -0.24 2.94 2.87 -0.06 2.20 1.85 173.2 172.8

HSH...OH₂ (46) -2.93 -2.91 0.02 3.33 3.38 0.05 2.29 2.03 175.3 172.8

HOH...S(CH₃)₂ (47) -3.56 -3.48 0.08 3.12 3.35 0.23 3.13 2.38 97.7 170.8

3.12 3.35 0.23 3.13 3.62 97.7 66.4

OHH...CH₃SSCH₃, cyclic (48) -3.78 -3.22 0.56 3.38 3.55 0.17 2.84 2.58 147.0 174.6

HOH...Thiophene (49) -2.66 -2.71 -0.05 3.59 3.69 0.10 3.50 3.03 108.4 126.8

3.59 3.69 0.10 3.33 3.34 121.0 103.6

HOH...SHC₆H₅ (50) -2.20 -3.45 -1.25 4.56 4.37 -0.19 4.27 3.55 132.4 144.2

HSH...SH₂ (51) -0.96 -1.25 -0.29 4.15 4.02 -0.13 3.19 2.70 175.5 167.3

HOH...SH₂ (52) -2.27 -2.00 0.27 3.47 3.49 0.02 2.83 2.55 175.5 163.2

CH3COOH...NH3, bidentate (53) -11.94 -11.58 0.36 2.63 2.66 0.03 1.90 1.66 168.3 174.3

2.89 3.02 0.12 2.53 2.43 119.0 115.2

HOH...PyridineN-oxide (54) -10.69 -10.61 0.08 2.63 2.64 0.01 1.94 1.65 161.0 178.6

2.66 2.88 0.22 2.18 2.10 130.2 135.1

HOH...FCH3 (59) -4.87 -4.48 0.39 2.70 2.66 -0.04 2.06 1.69 153.9 172.7

HOH...Chloropropane (58) -3.09 -2.84 0.25 3.34 3.35 0.01 2.82 2.45 143.5 153.9

H₂NH...O(CH₃)₂ (59) -3.12 -3.43 -0.31 3.00 3.00 0.00 2.32 1.97 155.9 173.9

Methylammonium...OH₂ (60) -19.30 -21.17 -1.87 2.70 2.62 -0.08 1.79 1.57 173.8 176.7

Guanidinium...OHH (61) -18.48 -19.02 -0.54 2.85 2.78 -0.07 2.08 1.87 147.7 146.8

2.85 2.78 -0.07 2.08 1.87 147.7 146.8

Imidazolium...OH2 (62) -16.95 -17.60 -0.65 2.71 2.62 -0.08 1.81 1.59 174.5 173.4

Formamidinium...OH₂ (63) -16.98 -18.75 -1.77 2.71 2.61 -0.10 1.91 1.57 148.7 177.2 Formamidinium...OH₂, cyclic C_2v (64) -19.59 -19.71 -0.12 2.83 2.78 -0.05 2.09 1.89 142.6 143.6

2.83 2.78 -0.05 2.09 1.89 142.6 143.6

Formaldehydeiminium...OH₂ (65) -19.98 -21.65 -1.67 2.66 2.65 -0.01 1.78 1.61 163.4 176.6 OHH...(-)O₂CCH₃, bidentate (66) -21.85 -22.62 -0.77 2.77 2.74 -0.03 2.06 1.87 142.9 145.7

2.78 2.74 -0.03 2.08 1.87 141.8 145.7

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

[image:26.792.66.732.122.532.2]

TABLE SM-III.

_________________________________________________________________________________

MMFF94s vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.61 -0.14 2.73 2.75 0.02 2.03 1.78 172.3 170.4

HOH...HOH, cyclic C_s (2) -5.02 -4.91 0.11 2.58 2.78 0.19 2.31 2.19 111.8 117.0

2.58 2.78 0.19 2.31 2.19 111.8 117.0

HOH...OHCH₃ (3) -6.10 -6.33 -0.23 2.72 2.73 0.02 2.01 1.76 169.0 168.7

CH3OH...OH2 (4) -6.15 -6.15 0.00 2.72 2.75 0.03 2.01 1.76 174.9 179.9

CH₃OH...OHCH₃ (5) -6.09 -6.04 0.05 2.71 2.73 0.02 2.00 1.74 174.6 177.0

HOH...O(CH₃)₂ (6) -5.84 -5.98 -0.14 2.71 2.77 0.06 2.02 1.81 163.9 166.7

C6H5OH...OH2 (7) -8.10 -8.45 -0.35 2.67 2.69 0.02 1.95 1.72 174.0 167.5

HOH...OHC₆H₅ (8) -5.18 -5.08 0.10 2.79 2.83 0.04 2.12 1.89 160.8 159.9

t-Vinyl alcohol...OH₂ (9) -8.18 -8.48 -0.30 2.65 2.68 0.02 1.93 1.69 175.0 176.1 HOH...t-Vinyl alcohol (10) -5.16 -5.46 -0.30 2.79 2.81 0.02 2.11 1.87 163.2 160.4

HOH...Furan (11) -4.00 -3.78 0.22 2.78 2.88 0.10 2.22 1.97 141.6 155.4

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -17.09 0.01 2.57 2.62 0.05 1.83 1.63 175.9 169.2

2.57 2.62 0.05 1.83 1.63 175.9 169.2

H3CCOOH...OHH (13) -10.94 -11.70 -0.76 2.58 2.64 0.07 1.90 1.67 156.3 163.4

2.61 2.77 0.16 2.15 2.11 127.9 122.8

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -12.72 -1.49 2.54 2.61 0.07 1.80 1.61 171.5 175.4

2.61 2.60 -0.02 2.22 1.92 122.2 123.9

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -6.10 -1.20 2.97 2.94 -0.04 2.44 2.02 141.1 155.7

HOH...skew-Methyl vinyl ether (17) -5.20 -4.80 0.40 2.73 2.87 0.14 2.08 1.94 155.6 159.0 HOH...Methyl formate (=O) (18) -6.39 -6.84 -0.45 2.76 2.73 -0.03 2.06 1.75 167.0 177.6 HOH...Methyl formate (-O-) (19) -3.82 -2.62 1.20 2.78 2.95 0.17 2.24 2.12 138.7 142.0

HOH...Formaldehyde (20) -5.81 -6.74 -0.93 2.72 2.71 0.00 2.11 1.74 147.6 170.5

HOH...Acetone (21) -6.87 -7.06 -0.19 2.74 2.71 -0.03 2.06 1.73 163.1 173.1

t-NMA...OH₂ (22) -5.97 -6.87 -0.90 2.87 2.84 -0.03 2.12 1.81 178.3 179.9

HOH...t-NMA (23) -8.03 -8.25 -0.22 2.70 2.70 0.00 2.00 1.72 167.6 174.3

Formamide dimer, cyclic (24) -14.78 -12.26 2.52 2.76 2.81 0.06 2.00 1.79 171.6 173.4

2.76 2.81 0.06 2.00 1.79 171.5 173.4

Formamide dimer, parallel (25) -8.12 -7.69 0.43 2.80 2.76 -0.03 2.09 1.74 156.7 174.1

t-NMA dimer, antiparallel (26) -7.70 -9.06 -1.36 2.83 2.76 -0.07 2.08 1.75 171.8 166.8

t-NMA antiparallel stacked (27) -3.86 -5.33 -1.47 3.65 3.64 -0.01 3.88 3.54 87.9 88.0

3.67 3.64 -0.02 3.88 3.54 88.9 88.0

HOH...N-Methylformamide (28) -7.90 -8.14 -0.24 2.71 2.71 0.00 2.01 1.73 164.7 174.9 N-Methylformamide...OH2 (29) -6.05 -6.90 -0.85 2.84 2.83 -0.01 2.09 1.80 173.8 175.5

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -8.30 -0.09 2.62 2.70 0.08 1.94 1.72 159.2 177.0 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -4.26 -0.16 2.82 2.84 0.03 2.12 1.87 168.7 178.2 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -3.02 0.49 3.01 3.11 0.10 2.60 2.40 123.9 125.4

3.01 3.11 0.10 2.61 2.40 123.8 125.4

H₂NH...NH₃, linear C_s (33) -3.38 -3.67 -0.29 3.15 3.03 -0.12 2.42 2.00 179.0 178.1

3.15 3.03 -0.12 3.64 3.36 69.8 62.7

HOH...NH3 (34) -7.22 -6.83 0.39 2.80 2.80 0.00 2.09 1.82 176.4 173.9

Imidazole...OH₂ (36) -7.00 -7.91 -0.91 2.79 2.82 0.04 2.03 1.81 178.2 175.6

HOH...Imidazole (37) -7.77 -7.93 -0.16 2.73 2.75 0.01 2.10 1.81 151.2 158.6

Indole...OH₂ (38) -6.33 -6.51 -0.18 2.81 2.86 0.05 2.07 1.84 168.3 179.7

Pyrrole...OH2 (39) -5.89 -6.28 -0.39 2.82 2.86 0.04 2.07 1.84 180.0 180.0

HOH...Pyridine (40) -6.63 -7.10 -0.47 2.77 2.79 0.02 2.12 1.85 155.8 158.9

Formamidine...H2O, cyclic (41) -11.03 -10.68 0.35 2.81 2.97 0.16 2.20 2.13 143.3 137.8

2.70 2.77 0.07 2.06 1.80 151.4 167.5

HOH...Formaldehydeimine (42) -6.74 -7.95 -1.21 2.76 2.74 -0.02 2.11 1.77 154.0 167.6

Guanidine...OHH (43) -7.96 -7.02 0.94 2.88 2.88 0.00 2.25 1.88 145.4 165.7

2.77 3.22 0.46 2.21 3.84 141.1 45.0

Vinylamine...OH2 (44) -3.80 -4.23 -0.43 3.04 2.88 -0.16 2.19 1.85 164.2 176.9

Aniline...OH₂ (45) -4.62 -4.54 0.08 2.94 2.88 -0.06 2.20 1.86 173.2 174.9

HSH...OH₂ (46) -2.93 -2.91 0.02 3.33 3.38 0.05 2.29 2.03 175.3 172.8

HOH...S(CH₃)₂ (47) -3.56 -3.48 0.08 3.12 3.35 0.23 3.13 2.38 97.7 170.8

3.12 3.35 0.23 3.13 3.62 97.7 66.4

OHH...CH₃SSCH₃, cyclic (48) -3.78 -3.22 0.56 3.38 3.55 0.17 2.84 2.58 147.0 174.6

HOH...Thiophene (49) -2.66 -2.71 -0.05 3.59 3.69 0.10 3.50 3.03 108.4 126.8

3.59 3.69 0.10 3.33 3.34 121.0 103.6

HOH...SHC₆H₅ (50) -2.20 -3.45 -1.25 4.56 4.37 -0.19 4.27 3.55 132.4 144.2

HSH...SH₂ (51) -0.96 -1.25 -0.29 4.15 4.02 -0.13 3.19 2.70 175.5 167.3

HOH...SH₂ (52) -2.27 -2.00 0.27 3.47 3.49 0.02 2.83 2.55 175.5 163.2

CH3COOH...NH3, bidentate (53) -11.94 -11.58 0.36 2.63 2.66 0.03 1.90 1.66 168.3 174.3

2.89 3.02 0.12 2.53 2.43 119.0 115.2

HOH...PyridineN-oxide (54) -10.69 -10.61 0.08 2.63 2.64 0.01 1.94 1.65 161.0 178.6

2.66 2.88 0.22 2.18 2.10 130.2 135.1

HOH...FCH3 (59) -4.87 -4.48 0.39 2.70 2.66 -0.04 2.06 1.69 153.9 172.7

HOH...Chloropropane (58) -3.09 -2.84 0.25 3.34 3.35 0.01 2.82 2.45 143.5 153.9

H₂NH...O(CH₃)₂ (59) -3.12 -3.43 -0.31 3.00 3.00 0.00 2.32 1.97 155.9 173.9

Methylammonium...OH₂ (60) -19.30 -21.17 -1.87 2.70 2.62 -0.08 1.79 1.57 173.8 176.7

Guanidinium...OHH (61) -18.48 -19.02 -0.54 2.85 2.78 -0.07 2.08 1.87 147.7 146.8

2.85 2.78 -0.07 2.08 1.87 147.7 146.8

Imidazolium...OH2 (62) -16.95 -17.60 -0.65 2.71 2.62 -0.08 1.81 1.59 174.5 173.4

Formamidinium...OH₂ (63) -16.98 -18.75 -1.77 2.71 2.61 -0.10 1.91 1.57 148.7 177.2 Formamidinium...OH₂, cyclic C_2v (64) -19.59 -19.71 -0.12 2.83 2.78 -0.05 2.09 1.89 142.6 143.6

2.83 2.78 -0.05 2.09 1.89 142.6 143.6

Formaldehydeiminium...OH₂ (65) -19.98 -21.65 -1.67 2.66 2.65 -0.01 1.78 1.61 163.4 176.6 OHH...(-)O₂CCH₃, bidentate (66) -21.85 -22.62 -0.77 2.77 2.74 -0.03 2.06 1.87 142.9 145.7

2.78 2.74 -0.03 2.08 1.87 141.8 145.7

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

[image:30.792.79.736.125.530.2]

TABLE SM-IV.

_________________________________________________________________________________

CFF95 vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -5.40 1.07 2.73 2.90 0.17 2.03 1.93 172.3 169.6

HOH...HOH, cyclic C_s (2) -5.02 -4.26 0.76 2.58 2.88 0.30 2.31 2.25 111.8 121.4

2.58 2.88 0.30 2.31 2.25 111.8 121.4

HOH...OHCH₃ (3) -6.10 -4.61 1.49 2.72 2.93 0.22 2.01 1.97 169.0 168.1

CH3OH...OH2 (4) -6.15 -6.53 -0.38 2.72 2.84 0.11 2.01 1.86 174.9 179.0

CH₃OH...OHCH₃ (5) -6.09 -5.65 0.44 2.71 2.86 0.15 2.00 1.89 174.6 179.0

HOH...O(CH₃)₂ (6) -5.84 -2.93 2.91 2.71 3.08 0.37 2.02 2.11 163.9 176.3

C6H5OH...OH2 (7) -8.10 -6.28 1.82 2.67 2.88 0.21 1.95 1.91 174.0 173.8

HOH...OHC₆H₅ (8) -5.18 -3.97 1.21 2.79 3.03 0.24 2.12 2.10 160.8 159.3

t-Vinyl alcohol...OH₂ (9) -8.18 -6.32 1.86 2.65 2.85 0.19 1.93 1.87 175.0 179.3

HOH...t-Vinyl alcohol (10) -5.16 -5.37 -0.21 2.79 2.90 0.12 2.11 1.96 163.2 162.1

HOH...Furan (11) -4.00 -3.86 0.14 2.78 3.14 0.36 2.22 2.22 141.6 156.6

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -10.57 6.53 2.57 2.88 0.31 1.83 1.91 175.9 169.0

2.57 2.88 0.31 1.83 1.91 175.9 169.0

H3CCOOH...OHH (13) -10.94 -9.00 1.94 2.58 2.80 0.22 1.90 1.83 156.3 168.3

2.61 3.03 0.42 2.15 2.48 127.9 115.5

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -8.97 2.26 2.54 2.80 0.26 1.80 1.84 171.5 167.3

2.61 2.88 0.27 2.22 2.29 122.2 118.3

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -4.20 0.70 2.97 3.16 0.19 2.44 2.21 141.1 163.8

HOH...skew-Methyl vinyl ether (17) -5.20 -3.78 1.42 2.73 3.03 0.30 2.08 2.09 155.6 160.8 HOH...Methyl formate (=O) (18) -6.39 -4.58 1.81 2.76 2.98 0.22 2.06 2.00 167.0 179.2 HOH...Methyl formate (-O-) (19) -3.82 -4.58 -0.76 2.78 4.30 1.52 2.24 3.49 138.7 141.3

HOH...Formaldehyde (20) -5.81 -3.85 1.96 2.72 2.98 0.27 2.11 2.03 147.6 166.8

HOH...Acetone (21) -6.87 -4.13 2.74 2.74 2.99 0.25 2.06 2.01 163.1 179.9

t-NMA...OH₂ (22) -5.97 -7.41 -1.44 2.87 2.91 0.04 2.12 1.89 178.3 179.1

HOH...t-NMA (23) -8.03 -5.67 2.36 2.70 2.95 0.25 2.00 1.98 167.6 172.2

Formamide dimer, cyclic (24) -14.78 -10.02 4.76 2.76 2.99 0.23 2.00 1.97 171.6 177.5

2.76 2.99 0.23 2.00 1.97 171.5 177.5

Formamide dimer, parallel (25) -8.12 -6.49 1.63 2.80 2.98 0.19 2.09 2.06 156.7 149.8

t-NMA dimer, antiparallel (26) -7.70 -7.88 -0.18 2.83 2.95 0.12 2.08 1.95 171.8 167.4

t-NMA antiparallel stacked (27) -3.86 -5.28 -1.42 3.65 3.84 0.19 3.88 3.69 87.9 91.1

3.67 3.84 0.17 3.88 3.69 88.9 91.1

HOH...N-Methylformamide (28) -7.90 -5.66 2.23 2.71 2.95 0.24 2.01 1.98 164.7 172.1

N-Methylformamide...OH2 (29) -6.05 -7.43 -1.38 2.84 2.90 0.06 2.09 1.88 173.8 177.0

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -7.50 0.71 2.62 2.82 0.20 1.94 1.88 159.2 160.3 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -8.29 -4.19 2.82 2.82 0.01 2.12 3.49 168.7 40.3 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -1.29 2.22 3.01 3.16 0.15 2.60 2.42 123.9 130.0

3.01 3.16 0.15 2.61 2.42 123.8 130.0

H₂NH...NH₃, linear C_s (33) -3.38 -1.38 2.00 3.15 3.20 0.05 2.42 2.19 179.0 177.7

3.15 3.20 0.05 3.64 3.25 69.8 78.4

HOH...NH3 (34) -7.22 -3.75 3.47 2.80 2.97 0.18 2.09 2.00 176.4 173.6

Imidazole...OH₂ (36) -7.00 -7.81 -0.81 2.79 2.85 0.06 2.03 1.82 178.2 178.0

HOH...Imidazole (37) -7.77 -6.05 1.72 2.73 3.14 0.41 2.10 2.25 151.2 150.0

Indole...OH₂ (38) -6.33 -6.82 -0.49 2.81 2.88 0.07 2.07 1.84 168.3 175.7

Pyrrole...OH2 (39) -5.89 -6.28 -0.39 2.82 2.89 0.07 2.07 1.85 180.0 180.0

HOH...Pyridine (40) -6.63 -4.25 2.38 2.77 3.20 0.42 2.12 2.32 155.8 148.8

Formamidine...H2O, cyclic (41) -11.03 -8.51 2.52 2.81 2.98 0.17 2.20 2.11 143.3 142.5

2.70 2.90 0.20 2.06 1.92 151.4 171.2

HOH...Formaldehydeimine (42) -6.74 -5.91 0.83 2.76 2.90 0.14 2.11 1.92 154.0 179.6

Guanidine...OHH (43) -7.96 -7.00 0.96 2.88 3.01 0.13 2.25 2.10 145.4 148.2

2.77 2.97 0.20 2.21 2.06 141.1 152.8

Vinylamine...OH2 (44) -3.80 -4.33 -0.53 3.04 2.98 -0.06 2.19 1.97 164.2 177.0

Aniline...OH₂ (45) -4.62 -5.17 -0.55 2.94 2.93 -0.01 2.20 1.91 173.2 175.0

HSH...OH₂ (46) -2.93 -2.19 0.74 3.33 3.58 0.25 2.29 2.84 175.3 113.4

HOH...S(CH₃)₂ (47) -3.56 -2.05 1.51 3.12 3.28 0.16 3.13 2.30 97.7 178.2

3.12 3.28 0.16 3.13 3.64 97.7 60.6

OHH...CH₃SSCH₃, cyclic (48) -3.78 -1.71 2.07 3.38 3.47 0.09 2.84 2.50 147.0 172.9

HOH...Thiophene (49) -2.66 -4.36 -1.70 3.59 3.63 0.04 3.50 3.57 108.4 85.7

3.59 3.63 0.04 3.33 2.91 121.0 131.4

HOH...SHC₆H₅ (50) -2.20 -4.38 -2.18 4.56 4.40 -0.16 4.27 3.77 132.4 125.0

HSH...SH₂ (51) -0.96 -1.23 -0.26 4.15 3.77 -0.38 3.19 3.02 175.5 114.4

HOH...SH₂ (52) -2.27 -2.75 -0.48 3.47 3.09 -0.38 2.83 2.13 175.5 167.5

CH3COOH...NH3, bidentate (53) -11.94 -6.04 5.90 2.63 2.86 0.23 1.90 1.88 168.3 177.6

2.89 3.27 0.37 2.53 2.74 119.0 112.8

HOH...PyridineN-oxide (54) -10.69 -7.20 3.49 2.63 2.87 0.24 1.94 1.89 161.0 177.3

2.66 3.58 0.92 2.18 3.99 130.2 58.3

HOH...FCH3 (59) -4.87 -1.69 3.17 2.70 3.09 0.39 2.06 2.13 153.9 169.7

HOH...Chloropropane (58) -3.09 -1.09 1.99 3.34 4.43 1.10 2.82 3.81 143.5 125.0

H₂NH...O(CH₃)₂ (59) -3.12 -1.18 1.94 3.00 3.36 0.36 2.32 2.35 155.9 179.8

Methylammonium...OH₂ (60) -19.30 -18.81 0.49 2.70 2.74 0.04 1.79 1.74 173.8 167.9

Guanidinium...OHH (61) -18.48 -16.40 2.08 2.85 2.96 0.11 2.08 2.02 147.7 152.4

2.85 2.96 0.11 2.08 2.02 147.7 152.4

Imidazolium...OH2 (62) -16.95 -15.95 1.00 2.71 2.78 0.07 1.81 1.74 174.5 172.4

OHH...(-)O₂CCH₃, bidentate (66) -21.85 -17.22 4.63 2.77 2.86 0.09 2.06 2.00 142.9 143.9

2.78 2.86 0.08 2.08 2.00 141.8 143.9

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

[image:34.792.81.742.125.530.2]

TABLE SM-IV.

_________________________________________________________________________________

CVFF vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.40 0.07 2.73 2.76 0.03 2.03 1.79 172.3 173.7

HOH...HOH, cyclic C_s (2) -5.02 -4.74 0.28 2.58 2.81 0.23 2.31 2.17 111.8 122.3

2.58 2.81 0.23 2.31 2.17 111.8 122.3

HOH...OHCH₃ (3) -6.10 -4.41 1.69 2.72 2.81 0.09 2.01 1.85 169.0 168.0

CH3OH...OH2 (4) -6.15 -6.78 -0.63 2.72 2.66 -0.06 2.01 1.68 174.9 176.0

CH₃OH...OHCH₃ (5) -6.09 -5.03 1.06 2.71 2.69 -0.02 2.00 1.72 174.6 174.9

HOH...O(CH₃)₂ (6) -5.84 -5.09 0.75 2.71 2.79 0.08 2.02 1.82 163.9 173.5

C6H5OH...OH2 (7) -8.10 -7.57 0.53 2.67 2.67 0.01 1.95 1.71 174.0 169.3

HOH...OHC₆H₅ (8) -5.18 -4.18 1.00 2.79 2.83 0.05 2.12 1.88 160.8 167.9

t-Vinyl alcohol...OH₂ (9) -8.18 -7.33 0.85 2.65 2.66 0.00 1.93 1.68 175.0 177.2

HOH...t-Vinyl alcohol (10) -5.16 -4.31 0.85 2.79 2.81 0.02 2.11 1.85 163.2 167.5

HOH...Furan (11) -4.00 -3.87 0.13 2.78 2.93 0.15 2.22 2.01 141.6 158.4

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -11.14 5.96 2.57 2.66 0.09 1.83 1.70 175.9 171.7

2.57 2.66 0.09 1.83 1.70 175.9 171.7

H3CCOOH...OHH (13) -10.94 -8.82 2.12 2.58 2.66 0.08 1.90 1.70 156.3 168.5

2.61 3.00 0.39 2.15 2.40 127.9 119.5

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -9.31 1.92 2.54 2.65 0.11 1.80 1.68 171.5 170.4

2.61 2.74 0.13 2.22 2.05 122.2 126.9

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -4.24 0.66 2.97 3.52 0.55 2.44 3.02 141.1 113.9

HOH...skew-Methyl vinyl ether (17) -5.20 -4.85 0.36 2.73 2.79 0.06 2.08 1.84 155.6 165.6 HOH...Methyl formate (=O) (18) -6.39 -6.19 0.20 2.76 2.75 -0.01 2.06 1.77 167.0 176.7 HOH...Methyl formate (-O-) (19) -3.82 -3.20 0.62 2.78 4.04 1.27 2.24 4.34 138.7 65.9

HOH...Formaldehyde (20) -5.81 -6.01 -0.20 2.72 2.75 0.03 2.11 1.78 147.6 174.5

HOH...Acetone (21) -6.87 -5.30 1.57 2.74 2.76 0.02 2.06 1.79 163.1 179.2

t-NMA...OH₂ (22) -5.97 -4.19 1.78 2.87 3.07 0.20 2.12 2.04 178.3 176.8

HOH...t-NMA (23) -8.03 -6.80 1.23 2.70 2.74 0.04 2.00 1.77 167.6 175.6

Formamide dimer, cyclic (24) -14.78 -6.53 8.25 2.76 3.00 0.24 2.00 1.97 171.6 175.9

2.76 3.00 0.24 2.00 1.97 171.5 175.9

Formamide dimer, parallel (25) -8.12 -5.23 2.89 2.80 3.08 0.29 2.09 2.28 156.7 133.4

t-NMA dimer, antiparallel (26) -7.70 -5.69 2.01 2.83 3.02 0.19 2.08 2.00 171.8 168.8

t-NMA antiparallel stacked (27) -3.86 -4.84 -0.98 3.65 4.00 0.35 3.88 3.82 87.9 92.7

3.67 4.00 0.33 3.88 3.82 88.9 92.7

HOH...N-Methylformamide (28) -7.90 -7.18 0.72 2.71 2.73 0.02 2.01 1.76 164.7 172.1

N-Methylformamide...OH2 (29) -6.05 -4.46 1.59 2.84 3.05 0.21 2.09 2.02 173.8 169.3

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -8.40 -0.19 2.62 2.64 0.02 1.94 1.68 159.2 168.0 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -9.06 -4.97 2.82 2.65 -0.17 2.12 3.31 168.7 40.6 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -0.46 3.05 3.01 3.69 0.69 2.60 2.92 123.9 132.8

3.01 3.69 0.69 2.61 2.92 123.8 132.8

H₂NH...NH₃, linear C_s (33) -3.38 -0.50 2.88 3.15 3.69 0.53 2.42 2.66 179.0 176.0

3.15 3.69 0.53 3.64 3.80 69.8 76.0

HOH...NH3 (34) -7.22 -1.99 5.23 2.80 3.18 0.39 2.09 2.22 176.4 173.1

Indole...OH₂ (38) -6.33 -2.59 3.74 2.81 3.09 0.28 2.07 2.06 168.3 176.9

Pyrrole...OH2 (39) -5.89 -2.28 3.61 2.82 3.11 0.29 2.07 2.07 180.0 180.0

HOH...Pyridine (40) -6.63 -3.36 3.27 2.77 3.48 0.70 2.12 3.26 155.8 95.0

Formamidine...H2O, cyclic (41) -11.03 -3.49 7.54 2.81 3.21 0.40 2.20 2.28 143.3 150.4

2.70 3.18 0.48 2.06 2.25 151.4 160.8

HOH...Formaldehydeimine (42) -6.74 -3.00 3.74 2.76 3.17 0.41 2.11 2.23 154.0 162.4

Guanidine...OHH (43) -7.96 -5.74 2.22 2.88 3.16 0.28 2.25 2.19 145.4 157.1

2.77 3.16 0.40 2.21 3.80 141.1 42.7

Vinylamine...OH2 (44) -3.80 -1.76 2.03 3.04 3.15 0.11 2.19 2.12 164.2 179.7

Aniline...OH₂ (45) -4.62 -2.82 1.80 2.94 3.12 0.18 2.20 2.09 173.2 179.9

HSH...OH₂ (46) -2.93 -0.98 1.95 3.33 3.48 0.15 2.29 2.94 175.3 102.6

HOH...S(CH3)2 (47) -3.56 -1.23 2.33 3.12 3.40 0.29 3.13 3.60 97.7 70.4

3.12 3.40 0.29 3.13 2.46 97.7 166.0

OHH...CH₃SSCH₃, cyclic (48) -3.78 -1.32 2.46 3.38 3.41 0.03 2.84 2.48 147.0 162.6

HOH...Thiophene (49) -2.66 -3.76 -1.10 3.59 3.49 -0.10 3.50 3.75 108.4 66.7

3.59 3.49 -0.10 3.33 2.79 121.0 129.3

HOH...SHC6H5 (50) -2.20 -3.45 -1.25 4.56 4.56 -0.01 4.27 3.99 132.4 120.4

HSH...SH₂ (51) -0.96 -0.46 0.50 4.15 3.51 -0.64 3.19 3.13 175.5 94.8

HOH...SH₂ (52) -2.27 -1.54 0.73 3.47 3.04 -0.43 2.83 2.09 175.5 171.7

CH3COOH...NH3, bidentate (53) -11.94 -2.95 8.99 2.63 3.05 0.42 1.90 2.09 168.3 176.2

2.89 3.43 0.53 2.53 2.84 119.0 116.9

HOH...PyridineN-oxide (54) -10.69 -3.53 7.16 2.63 3.82 1.19 1.94 4.26 161.0 57.4

MethylethylamineN-oxide...OHH( 55) -15.48 -16.58 -1.10 2.49 3.50 1.01 1.83 3.85 148.9 62.2

2.64 2.84 0.21 2.17 1.80 124.2 174.1

HOH...Chloropropane (58) -3.09 -3.16 -0.08 3.34 3.09 -0.25 2.82 2.12 143.5 178.1

H₂NH...O(CH₃)₂ (59) -3.12 -1.44 1.68 3.00 3.29 0.29 2.32 2.27 155.9 177.7

Methylammonium...OH₂ (60) -19.30 -17.49 1.81 2.70 2.81 0.11 1.79 1.76 173.8 177.2

Guanidinium...OHH (61) -18.48 -5.50 12.98 2.85 3.20 0.34 2.08 3.48 147.7 65.9

2.85 3.53 0.68 2.08 3.76 147.7 69.1

Imidazolium...OH₂ (62) -16.95 -13.21 3.74 2.71 2.86 0.16 1.81 1.82 174.5 175.5

Formamidinium...OH₂ (63) -16.98 -2.40 14.58 2.71 3.11 0.41 1.91 2.08 148.7 179.3

Formamidinium...OH₂, cyclic C2v (64) -19.59 -3.20 16.39 2.83 3.24 0.40 2.09 2.24 142.6 162.5

2.83 3.24 0.40 2.09 2.24 142.6 162.5

OHH...(-)O₂CCH₃, bidentate (66) -21.85 -22.84 -0.99 2.77 2.69 -0.07 2.06 1.81 142.9 147.2

2.78 2.69 -0.08 2.08 1.81 141.8 147.2

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

[image:38.792.78.736.125.529.2]

TABLE SM-VI.

_________________________________________________________________________________

MSI_CHARMm vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.83 -0.36 2.73 2.76 0.02 2.03 1.78 172.3 173.3

HOH...HOH, cyclic C_s (2) -5.02 -6.75 -1.73 2.58 2.76 0.18 2.31 1.78 111.8 177.5

2.58 2.76 0.18 2.31 3.21 111.8 53.9

HOH...OHCH₃ (3) -6.10 -6.24 -0.14 2.72 2.87 0.16 2.01 1.99 169.0 151.9

CH3OH...OH2 (4) -6.15 -5.19 0.96 2.72 2.97 0.25 2.01 2.02 174.9 171.7

CH₃OH...OHCH₃ (5) -6.09 -6.49 -0.39 2.71 2.77 0.06 2.00 1.84 174.6 163.0

HOH...O(CH₃)₂ (6) -5.84 -4.59 1.25 2.71 2.93 0.22 2.02 2.10 163.9 142.7

C6H5OH...OH2 (7) -8.10 -5.66 2.44 2.67 2.98 0.31 1.95 2.03 174.0 179.5

HOH...OHC₆H₅ (8) -5.18 -6.75 -1.57 2.79 2.87 0.08 2.12 2.00 160.8 150.2

t-Vinyl alcohol...OH₂ (9) -8.18 -6.25 1.93 2.65 2.95 0.29 1.93 1.99 175.0 179.1

HOH...t-Vinyl alcohol (10) -5.16 -5.06 0.10 2.79 2.87 0.08 2.11 2.15 163.2 130.4

HOH...Furan (11) -4.00 -3.36 0.64 2.78 3.25 0.46 2.22 2.78 141.6 110.9

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -3.56 13.54 2.57 2.89 0.32 1.83 1.94 175.9 170.4

2.57 2.89 0.32 1.83 1.94 175.9 170.4

H3CCOOH...OHH (13) -10.94 -6.30 4.64 2.58 3.22 0.64 1.90 2.40 156.3 144.0

2.61 2.82 0.21 2.15 1.99 127.9 143.4

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -4.15 7.08 2.54 3.16 0.62 1.80 2.21 171.5 174.9

2.61 2.74 0.12 2.22 1.96 122.2 135.6

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -7.25 -2.35 2.97 2.94 -0.03 2.44 2.05 141.1 154.5

HOH...skew-Methyl vinyl ether (17) -5.20 -4.79 0.41 2.73 2.90 0.17 2.08 2.13 155.6 135.7 HOH...Methyl formate (=O) (18) -6.39 -7.47 -1.08 2.76 2.90 0.14 2.06 1.97 167.0 162.0 HOH...Methyl formate (-O-) (19) -3.82 -5.68 -1.86 2.78 2.96 0.19 2.24 2.06 138.7 154.8

HOH...Formaldehyde (20) -5.81 -5.59 0.22 2.72 2.88 0.16 2.11 2.02 147.6 148.0

HOH...Acetone (21) -6.87 -6.18 0.70 2.74 2.91 0.17 2.06 1.98 163.1 161.1

t-NMA...OH₂ (22) -5.97 -5.20 0.77 2.87 3.11 0.25 2.12 2.11 178.3 179.3

HOH...t-NMA (23) -8.03 -6.87 1.16 2.70 2.90 0.20 2.00 1.99 167.6 158.0

Formamide dimer, cyclic (24) -14.78 -11.68 3.11 2.76 2.91 0.15 2.00 1.90 171.6 176.2

2.76 2.91 0.15 2.00 1.90 171.5 176.2

Formamide dimer, parallel (25) -8.12 -8.38 -0.26 2.80 2.85 0.05 2.09 1.95 156.7 147.1

t-NMA dimer, antiparallel (26) -7.70 -7.83 -0.13 2.83 2.82 -0.01 2.08 1.97 171.8 140.6

t-NMA antiparallel stacked (27) -3.86 -8.08 -4.22 3.65 3.39 -0.26 3.88 3.55 87.9 72.8

3.67 3.39 -0.28 3.88 3.55 88.9 72.8

HOH...N-Methylformamide (28) -7.90 -6.81 1.09 2.71 2.96 0.26 2.01 2.01 164.7 173.0

N-Methylformamide...OH2 (29) -6.05 -5.39 0.66 2.84 3.08 0.24 2.09 2.08 173.8 177.0

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -8.21 0.00 2.62 2.90 0.28 1.94 2.08 159.2 143.6 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -8.21 -4.11 2.82 2.90 0.09 2.12 3.46 168.7 48.2 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -5.60 -2.09 3.01 2.75 -0.26 2.60 2.03 123.9 125.8

3.01 2.75 -0.26 2.61 2.03 123.8 125.8

H₂NH...NH₃, linear C_s (33) -3.38 -4.52 -1.14 3.15 2.75 -0.40 2.42 2.03 179.0 125.8

3.15 2.75 -0.40 3.64 2.03 69.8 125.8

HOH...NH3 (34) -7.22 -6.39 0.82 2.80 2.96 0.16 2.09 2.02 176.4 162.9

Imidazole...OH₂ (36) -7.00 -10.83 -3.83 2.79 2.94 0.15 2.03 1.96 178.2 176.0

HOH...Imidazole (37) -7.77 -7.42 0.35 2.73 2.81 0.08 2.10 2.32 151.2 111.4

Indole...OH₂ (38) -6.33 -5.31 1.01 2.81 3.04 0.24 2.07 2.07 168.3 168.9

Pyrrole...OH2 (39) -5.89 -8.75 -2.85 2.82 2.97 0.15 2.07 1.98 180.0 180.0

HOH...Pyridine (40) -6.63 -4.56 2.08 2.77 2.99 0.22 2.12 2.31 155.8 127.1

Formamidine...H2O, cyclic (41) -11.03 -3.14 7.90 2.81 3.06 0.24 2.20 2.22 143.3 139.1

2.70 3.26 0.56 2.06 2.59 151.4 126.8

HOH...Formaldehydeimine (42) -6.74 -2.94 3.81 2.76 3.15 0.39 2.11 2.38 154.0 136.8

Guanidine...OHH (43) -7.96 -8.93 -0.97 2.88 2.96 0.08 2.25 2.03 145.4 151.7

2.77 2.97 0.21 2.21 3.60 141.1 43.1

Vinylamine...OH2 (44) -3.80 -3.89 -0.09 3.04 3.01 -0.03 2.19 3.45 164.2 56.3

Aniline...OH₂ (45) -4.62 -4.17 0.45 2.94 3.01 0.07 2.20 2.41 173.2 117.7

HSH...OH₂ (46) -2.93 -2.96 -0.03 3.33 3.08 -0.25 2.29 2.34 175.3 111.0

HOH...S(CH₃)₂ (47) -3.56 -1.68 1.87 3.12 3.24 0.13 3.13 2.77 97.7 111.2

3.12 3.24 0.13 3.13 2.78 97.7 110.7

OHH...CH₃SSCH₃, cyclic (48) -3.78 -1.20 2.59 3.38 3.42 0.04 2.84 3.19 147.0 95.4

HOH...Thiophene (49) -2.66 -4.61 -1.95 3.59 3.21 -0.39 3.50 3.13 108.4 86.2

3.59 3.21 -0.39 3.33 2.38 121.0 143.2

HOH...SHC₆H₅ (50) -2.20 -5.63 -3.43 4.56 3.30 -1.26 4.27 2.45 132.4 146.9

HSH...SH₂ (51) -0.96 -1.39 -0.43 4.15 3.22 -0.93 3.19 2.48 175.5 111.7

HOH...SH₂ (52) -2.27 -2.31 -0.04 3.47 3.15 -0.32 2.83 2.36 175.5 139.1

CH3COOH...NH3, bidentate (53) -11.94 -5.56 6.37 2.63 2.95 0.33 1.90 2.08 168.3 151.5

2.89 2.86 -0.03 2.53 1.89 119.0 157.9

2.66 3.10 0.44 2.18 3.20 130.2 75.0

HOH...FCH₃ (59) -4.87 -3.52 1.35 2.70 3.08 0.37 2.06 2.23 153.9 146.4

HOH...Chloropropane (58) -3.09 -2.72 0.37 3.34 3.55 0.21 2.82 2.72 143.5 145.4

H₂NH...O(CH₃)₂ (59) -3.12 -3.51 -0.39 3.00 3.02 0.02 2.32 2.01 155.9 178.4

Methylammonium...OH₂ (60) -19.30 -20.25 -0.95 2.70 2.76 0.06 1.79 1.88 173.8 140.5

Guanidinium...OHH (61) -18.48 -20.18 -1.70 2.85 2.88 0.03 2.08 1.97 147.7 148.1

2.85 2.88 0.03 2.08 1.97 147.7 148.1

Imidazolium...OH2 (62) -16.95 -17.18 -0.23 2.71 2.88 0.18 1.81 1.94 174.5 159.0

OHH...(-)O₂CCH₃, bidentate (66) -21.85 -17.23 4.62 2.77 2.93 0.16 2.06 2.11 142.9 140.6

2.78 2.93 0.15 2.08 2.11 141.8 140.6

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

[image:42.792.73.730.122.538.2]

TABLE SM-VII.

________________________________________________________________________________

CHARMM 22

a

vs. Scaled HF/-6-31G* Intermolecular-Interaction Energies and Distances.

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

b

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.83 -0.36 2.73 2.76 0.02 2.03 1.78 172.3 173.3

HOH...HOH, cyclic Cs (2) -5.02 -5.21 -0.19 2.58 2.77 0.19 2.31 2.13 111.8 122.5

2.58 2.77 0.19 2.31 2.13 111.8 122.4

HOH...OHCH₃ (3) -6.10 -7.06 -0.96 2.72 2.79 0.07 2.01 1.82 169.0 172.7

CH₃OH...OH₂ (4) -6.15 -6.64 -0.49 2.72 2.77 0.04 2.01 1.79 174.9 178.2

CH3OH...OHCH3 (5) -6.09 -6.99 -0.90 2.71 2.80 0.09 2.00 1.82 174.6 178.1

HOH...O(CH₃)₂ (6) -5.84 -6.50 -0.66 2.71 2.81 0.10 2.02 1.84 163.9 175.9

C₆H₅OH...OH₂ (7) -8.10 -8.08 0.03 2.67 2.75 0.08 1.95 1.79 174.0 171.9

HOH...OHC6H5 (8) -5.18 -5.34 -0.16 2.79 2.84 0.05 2.12 1.89 160.8 167.1

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -14.06 3.04 2.57 2.70 0.13 1.83 1.74 175.9 169.4

2.57 2.70 0.13 1.83 1.74 175.9 169.4

H3CCOOH...OHH (13) -10.94 -10.16 0.77 2.58 2.76 0.18 1.90 1.83 156.3 158.8

2.61 2.78 0.17 2.15 1.98 127.9 137.0

t-NMA...OH₂ (22) -5.97 -6.16 -0.19 2.87 2.91 0.04 2.12 1.90 178.3 179.1

HOH...t-NMA (23) -8.03 -8.37 -0.34 2.70 2.70 0.00 2.00 1.73 167.6 173.9

Formamide dimer, cyclic (24) -14.78 -12.65 2.13 2.76 2.82 0.06 2.00 1.81 171.6 179.2

2.76 2.82 0.06 2.00 1.81 171.5 179.2

Formamide dimer, parallel (25) -8.12 -7.67 0.45 2.80 2.81 0.01 2.09 1.84 156.7 159.4

t-NMA dimer, antiparallel (26) -7.70 -8.06 -0.36 2.83 2.84 0.01 2.08 1.85 171.8 166.4

3.01 3.04 0.03 2.61 2.28 123.8 131.2 H₂NH...NH₃, linear C_s (33) -3.38 -3.60 -0.22 3.15 3.04 -0.11 2.42 2.03 179.0 177.4

3.15 3.04 -0.11 3.64 3.09 69.8 77.7

HOH...NH3 (34) -7.22 -6.67 0.54 2.80 2.84 0.04 2.09 1.87 176.4 175.8

HOH...NH₂CH₃ (35) -7.07 -7.61 -0.54 2.80 2.84 0.05 2.09 1.87 175.9 173.3

Imidazole...OH₂ (36) -7.00 -6.85 0.16 2.79 2.87 0.08 2.03 1.85 178.2 176.9

HOH...Imidazole (37) -7.77 -8.44 -0.67 2.73 2.84 0.11 2.10 1.87 151.2 172.8

Indole...OH₂ (38) -6.33 -5.07 1.26 2.81 2.89 0.09 2.07 1.90 168.3 178.8

HSH...OH2 (46) -2.93 -3.19 -0.26 3.33 3.31 -0.02 2.29 1.99 175.3 171.6

HOH...S(CH₃)₂ (47) -3.56 -2.70 0.86 3.12 3.37 0.25 3.13 3.75 97.7 59.5

3.12 3.37 0.25 3.13 2.41 97.7 176.7

OHH...CH3SSCH3, cyclic (48) -3.78 -2.78 1.00 3.38 3.46 0.08 2.84 2.66 147.0 140.5

HSH...SH₂ (51) -0.96 -1.66 -0.69 4.15 3.75 -0.40 3.19 2.44 175.5 168.0

HOH...SH₂ (52) -2.27 -2.30 -0.03 3.47 3.32 -0.16 2.83 2.37 175.5 167.7

CH₃COOH...NH₃, bidentate (53) -11.94 -9.23 2.70 2.63 2.81 0.18 1.90 1.86 168.3 168.0

2.89 3.02 0.13 2.53 2.28 119.0 129.6

H₂NH...O(CH₃)₂ (59) -3.12 -3.82 -0.70 3.00 3.02 0.02 2.32 2.01 155.9 175.9

Methylammonium...OH2 (60) -19.30 -19.83 -0.53 2.70 2.75 0.05 1.79 1.69 173.8 177.2

Guanidinium...OHH (61) -18.48 -18.63 -0.15 2.85 2.89 0.04 2.08 1.96 147.7 152.6

2.85 2.89 0.04 2.08 1.96 147.7 152.7

Imidazolium...OH₂ (62) -16.95 -16.83 0.12 2.71 2.75 0.04 1.81 1.72 174.5 178.3

OHH...(-)O₂CCH₃, bidentate (66) -21.85 -24.18 -2.33 2.77 2.67 -0.10 2.06 1.80 142.9 146.4

a

See text for a specification of cases in which "cloned" force field parameters were employed.

b

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -7.09 -0.62 2.73 2.81 0.07 2.03 1.85 172.3 171.2

HOH...HOH, cyclic C_s (2) -5.02 -5.89 -0.87 2.58 2.75 0.17 2.31 2.10 111.8 122.7

2.58 2.75 0.17 2.31 2.10 111.8 122.7

HOH...OHCH₃ (3) -6.10 -6.27 -0.17 2.72 2.80 0.08 2.01 1.84 169.0 171.2

CH3OH...OH2 (4) -6.15 -5.14 1.01 2.72 2.82 0.09 2.01 1.85 174.9 178.0

CH₃OH...OHCH₃ (5) -6.09 -4.73 1.36 2.71 2.81 0.10 2.00 1.85 174.6 172.3

HOH...O(CH₃)₂ (6) -5.84 -6.64 -0.80 2.71 2.79 0.08 2.02 1.83 163.9 172.5

C6H5OH...OH2 (7) -8.10 -7.54 0.56 2.67 2.78 0.11 1.95 1.81 174.0 175.6

HOH...OHC₆H₅ (8) -5.18 -5.41 -0.23 2.79 2.92 0.13 2.12 2.01 160.8 157.6

t-Vinyl alcohol...OH₂ (9) -8.18 -7.00 1.18 2.65 2.78 0.13 1.93 1.81 175.0 178.2

HOH...t-Vinyl alcohol (10) -5.16 -5.64 -0.48 2.79 2.83 0.04 2.11 1.90 163.2 161.5

HOH...Furan (11) -4.00 -4.32 -0.32 2.78 3.10 0.32 2.22 2.34 141.6 135.7

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -11.04 6.06 2.57 2.71 0.14 1.83 1.77 175.9 166.1

2.57 2.71 0.14 1.83 1.77 175.9 166.1

H3CCOOH...OHH (13) -10.94 -9.30 1.64 2.58 2.77 0.19 1.90 1.87 156.3 153.8

2.61 2.77 0.16 2.15 1.95 127.9 141.1

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -8.45 2.78 2.54 2.80 0.26 1.80 1.84 171.5 167.9

2.61 2.68 0.07 2.22 1.95 122.2 130.9

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -4.90 0.00 2.97 3.54 0.56 2.44 3.33 141.1 94.0

[image:45.792.79.735.125.530.2]

OHH...trans,trans-Oxalic acid, cyclic (16) -3.82 -4.88 -1.06 2.90 2.83 -0.07 2.27 2.03 155.0 139.3

3.21 2.93 -0.28 2.95 2.15 117.5 137.3

HOH...skew-Methyl vinyl ether (17) -5.20 -5.97 -0.77 2.73 2.84 0.10 2.08 1.90 155.6 161.4 HOH...Methyl formate (=O) (18) -6.39 -6.48 -0.09 2.76 2.76 0.00 2.06 1.79 167.0 174.6 HOH...Methyl formate (-O-) (19) -3.82 -3.43 0.39 2.78 2.85 0.08 2.24 1.92 138.7 163.0

HOH...Formaldehyde (20) -5.81 -6.06 -0.25 2.72 2.75 0.03 2.11 1.79 147.6 174.1

HOH...Acetone (21) -6.87 -6.29 0.58 2.74 2.75 0.01 2.06 1.79 163.1 179.1

t-NMA...OH₂ (22) -5.97 -5.57 0.40 2.87 2.90 0.03 2.12 1.88 178.3 177.3

HOH...t-NMA (23) -8.03 -8.75 -0.72 2.70 2.72 0.02 2.00 1.75 167.6 179.4

Formamide dimer, cyclic (24) -14.78 -15.04 -0.26 2.76 2.75 0.00 2.00 1.74 171.6 176.7

2.76 2.75 0.00 2.00 1.74 171.5 176.7

Formamide dimer, parallel (25) -8.12 -9.07 -0.95 2.80 2.73 -0.07 2.09 1.77 156.7 153.6

t-NMA dimer, antiparallel (26) -7.70 -6.87 0.83 2.83 2.79 -0.04 2.08 1.81 171.8 161.2

t-NMA antiparallel stacked (27) -3.86 -4.92 -1.06 3.65 3.43 -0.22 3.88 3.38 87.9 84.0

3.67 3.43 -0.24 3.88 3.38 88.9 84.0

HOH...N-Methylformamide (28) -7.90 -8.71 -0.81 2.71 2.73 0.02 2.01 1.76 164.7 179.3 N-Methylformamide...OH2 (29) -6.05 -5.57 0.48 2.84 2.89 0.05 2.09 1.88 173.8 175.3

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -7.99 0.22 2.62 2.77 0.15 1.94 1.89 159.2 149.6 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -7.70 -3.60 2.82 2.79 -0.02 2.12 3.43 168.7 42.1 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -4.64 -1.13 3.01 2.86 -0.15 2.60 2.10 123.9 129.6

3.01 2.86 -0.15 2.61 2.11 123.8 129.1

H₂NH...NH₃, linear C_s (33) -3.38 -4.65 -1.27 3.15 2.92 -0.23 2.42 1.92 179.0 163.7

3.15 2.92 -0.23 3.64 2.68 69.8 93.2

HOH...NH3 (34) -7.22 -7.46 -0.24 2.80 2.83 0.03 2.09 1.86 176.4 175.3

Indole...OH₂ (38) -6.33 -5.82 0.51 2.81 2.88 0.07 2.07 1.86 168.3 176.6

Pyrrole...OH2 (39) -5.89 -4.02 1.87 2.82 2.91 0.09 2.07 1.89 180.0 180.0

HOH...Pyridine (40) -6.63 -7.13 -0.50 2.77 2.86 0.09 2.12 1.93 155.8 161.8

Formamidine...H2O, cyclic (41) -11.03 -7.22 3.81 2.81 2.85 0.03 2.20 1.96 143.3 143.9

2.70 2.94 0.25 2.06 1.98 151.4 173.4

HOH...Formaldehydeimine (42) -6.74 -4.44 2.30 2.76 2.94 0.18 2.11 1.99 154.0 167.7

Guanidine...OHH (43) -7.96 -7.67 0.29 2.88 2.86 -0.02 2.25 2.20 145.4 121.7

2.77 2.86 0.09 2.21 2.12 141.1 131.9

Vinylamine...OH2 (44) -3.80 -4.40 -0.60 3.04 2.89 -0.15 2.19 1.86 164.2 178.0

Aniline...OH₂ (45) -4.62 -7.23 -2.61 2.94 2.89 -0.05 2.20 3.18 173.2 63.9

HSH...OH₂ (46) -2.93 -4.12 -1.19 3.33 3.26 -0.07 2.29 2.01 175.3 153.0

HOH...S(CH₃)₂ (47) -3.56 -3.39 0.17 3.12 3.44 0.33 3.13 2.52 97.7 161.6

3.12 3.44 0.33 3.13 3.98 97.7 50.2

OHH...CH₃SSCH₃, cyclic (48) -3.78 -3.32 0.46 3.38 3.45 0.07 2.84 2.55 147.0 155.6

HOH...Thiophene (49) -2.66 -4.86 -2.20 3.59 3.33 -0.27 3.50 2.70 108.4 123.5

3.59 3.33 -0.27 3.33 2.98 121.0 102.8

HOH...SHC₆H₅ (50) -2.20 -4.65 -2.45 4.56 4.09 -0.48 4.27 3.31 132.4 139.1

HSH...SH₂ (51) -0.96 -2.94 -1.98 4.15 3.46 -0.69 3.19 2.76 175.5 110.6

HOH...SH₂ (52) -2.27 -3.83 -1.56 3.47 3.44 -0.04 2.83 2.48 175.5 177.6

CH3COOH...NH3, bidentate (53) -11.94 -9.02 2.92 2.63 2.79 0.16 1.90 1.86 168.3 159.1

2.89 2.89 -0.01 2.53 2.02 119.0 141.2

HOH...PyridineN-oxide (54) -10.69 -7.78 2.91 2.63 3.15 0.52 1.94 3.61 161.0 54.6

2.66 2.94 0.28 2.18 2.07 130.2 147.9

HOH...FCH₃ (59) -4.87 -2.72 2.15 2.70 3.17 0.46 2.06 2.33 153.9 145.5

HOH...Chloropropane (58) -3.09 -2.91 0.18 3.34 3.38 0.04 2.82 2.54 143.5 146.1

H₂NH...O(CH₃)₂ (59) -3.12 -4.33 -1.21 3.00 2.91 -0.09 2.32 1.89 155.9 177.0

Methylammonium...OH₂ (60) -19.30 -20.60 -1.30 2.70 2.75 0.05 1.79 1.74 173.8 173.9

Guanidinium...OHH (61) -18.48 -19.05 -0.57 2.85 2.83 -0.02 2.08 1.91 147.7 148.3

2.85 2.83 -0.02 2.08 1.91 147.7 148.3

Imidazolium...OH₂ (62) -16.95 -14.00 2.95 2.71 2.80 0.10 1.81 1.80 174.5 165.5

Formamidinium...OH₂ (63) -16.98 -17.79 -0.81 2.71 2.77 0.06 1.91 1.75 148.7 173.3 Formamidinium...OH₂, cyclic C2v (64) -19.59 -19.91 -0.32 2.83 2.86 0.02 2.09 1.97 142.6 144.1

2.83 2.80 -0.03 2.09 1.90 142.6 145.2

Formaldehydeiminium...OH₂ (65) -19.98 -22.24 -2.26 2.66 2.73 0.07 1.78 1.72 163.4 175.3 OHH...(-)O₂CCH₃, bidentate (66) -21.85 -22.25 -0.40 2.77 2.69 -0.08 2.06 1.85 142.9 142.0

2.78 2.69 -0.09 2.08 1.85 141.8 142.0

a

For representational drawings of the dimer structures, see Figure 1 of: T. A. Halgren,

J. Comput. Chem.

,

17

, 520-552

Energy (kcal/mol)

X...Z distance, Å

H...Z distance

X–H...Z angle

Dimer (Structure Number)

a

SQM

FF

Diff SQM FF

Diff SQM FF

QM

FF

HOH...OH2 (1) -6.47 -6.84 -0.37 2.73 2.73 0.00 2.03 1.76 172.3 173.5

HOH...HOH, cyclic C_s (2) -5.02 -5.05 -0.03 2.58 2.78 0.19 2.31 2.14 111.8 122.3

2.58 2.78 0.19 2.31 2.14 111.8 122.3

HOH...OHCH₃ (3) -6.10 -6.78 -0.68 2.72 2.73 0.01 2.01 1.76 169.0 172.9

CH3OH...OH2 (4) -6.15 -7.46 -1.31 2.72 2.69 -0.03 2.01 1.72 174.9 179.5

CH₃OH...OHCH₃ (5) -6.09 -7.64 -1.55 2.71 2.69 -0.02 2.00 1.71 174.6 178.3

HOH...O(CH₃)₂ (6) -5.84 -5.75 0.09 2.71 2.74 0.03 2.02 1.78 163.9 173.0

C6H5OH...OH2 (7) -8.10 -7.50 0.60 2.67 2.71 0.04 1.95 1.74 174.0 175.2

HOH...OHC₆H₅ (8) -5.18 -7.23 -2.05 2.79 2.73 -0.06 2.12 1.77 160.8 169.5

t-Vinyl alcohol...OH₂ (9) -8.18 -8.30 -0.12 2.65 2.68 0.03 1.93 1.70 175.0 179.7 HOH...t-Vinyl alcohol (10) -5.16 -6.14 -0.98 2.79 2.77 -0.02 2.11 1.82 163.2 166.9

HOH...Furan (11) -4.00 -2.89 1.11 2.78 3.43 0.65 2.22 2.76 141.6 127.5

H₃CCOOH...HOOCCH₃, cyclic (12) -17.10 -13.73 3.37 2.57 2.71 0.14 1.83 1.75 175.9 168.8

2.57 2.71 0.14 1.83 1.75 175.9 168.8

H3CCOOH...OHH (13) -10.94 -10.41 0.53 2.58 2.66 0.09 1.90 1.70 156.3 170.2

2.61 3.02 0.42 2.15 2.53 127.9 111.6

trans,trans-Oxalic acid...OHH, cyclic (14) -11.23 -8.55 2.68 2.54 2.69 0.15 1.80 1.74 171.5 164.3

2.61 2.75 0.14 2.22 2.21 122.2 114.4

OHH...cis,cis-Oxalic acid, cyclic (15) -4.90 -4.27 0.63 2.97 2.99 0.02 2.44 2.10 141.1 153.8

[image:49.792.79.735.124.529.2]

OHH...trans,trans-Oxalic acid, cyclic (16) -3.82 -4.01 -0.19 2.90 2.92 0.02 2.27 2.06 155.0 147.8

3.21 3.19 -0.02 2.95 2.48 117.5 130.7

HOH...skew-Methyl vinyl ether (17) -5.20 -3.96 1.24 2.73 2.86 0.13 2.08 1.91 155.6 167.1 HOH...Methyl formate (=O) (18) -6.39 -5.74 0.65 2.76 2.77 0.02 2.06 1.80 167.0 179.6 HOH...Methyl formate (-O-) (19) -3.82 -3.27 0.55 2.78 2.91 0.13 2.24 2.03 138.7 150.7

HOH...Formaldehyde (20) -5.81 -5.49 0.32 2.72 2.77 0.05 2.11 1.80 147.6 179.7

HOH...Acetone (21) -6.87 -4.90 1.97 2.74 2.79 0.05 2.06 1.82 163.1 178.1

t-NMA...OH₂ (22) -5.97 -8.73 -2.76 2.87 2.78 -0.09 2.12 1.75 178.3 179.5

HOH...t-NMA (23) -8.03 -7.56 0.47 2.70 2.73 0.02 2.00 1.76 167.6 174.1

Formamide dimer, cyclic (24) -14.78 -16.00 -1.22 2.76 2.75 -0.01 2.00 1.72 171.6 179.5

2.76 2.75 -0.01 2.00 1.72 171.5 179.5

Formamide dimer, parallel (25) -8.12 -9.91 -1.79 2.80 2.75 -0.04 2.09 1.76 156.7 161.0

t-NMA dimer, antiparallel (26) -7.70 -10.97 -3.27 2.83 2.75 -0.08 2.08 1.74 171.8 170.5

t-NMA antiparallel stacked (27) -3.86 -6.64 -2.78 3.65 3.76 0.10 3.88 3.72 87.9 84.0

3.67 3.76 0.09 3.88 3.72 88.9 84.0

HOH...N-Methylformamide (28) -7.90 -7.87 0.03 2.71 2.72 0.01 2.01 1.75 164.7 171.9

N-Methylformamide...OH2 (29) -6.05 -8.51 -2.46 2.84 2.78 -0.06 2.09 1.75 173.8 177.7

t-N-OH,N-Meacetamide...OH₂ (30) -8.21 -9.32 -1.11 2.62 2.72 0.10 1.94 1.83 159.2 151.1 HOH...t-N-OH,N-Methylacetamide (31) -4.10 -9.97 -5.87 2.82 2.67 -0.14 2.12 3.33 168.7 40.5 H₂NH...HNH₂, cyclic C_2h (32) -3.51 -4.07 -0.56 3.01 2.90 -0.11 2.60 2.13 123.9 131.0

3.01 2.90 -0.11 2.61 2.13 123.8 131.0

H₂NH...NH₃, linear C_s (33) -3.38 -4.53 -1.15 3.15 2.89 -0.26 2.42 1.87 179.0 176.9

3.15 2.89 -0.26 3.64 2.96 69.8 76.5

HOH...NH3 (34) -7.22 -7.54 -0.32 2.80 2.74 -0.05 2.09 1.77 176.4 176.4

Indole...OH₂ (38) -6.33 -7.97 -1.64 2.81 2.75 -0.05 2.07 1.72 168.3 179.7

Pyrrole...OH2 (39) -5.89 -7.60 -1.71 2.82 2.76 -0.06 2.07 1.72 180.0 180.0

HOH...Pyridine (40) -6.63 -5.72 0.91 2.77 2.87 0.10 2.12 1.91 155.8 167.6

Formamidine...H2O, cyclic (41) -11.03 -7.91 3.12 2.81 2.84 0.03 2.20 1.96 143.3 143.0

2.70 2.89 0.19 2.06 1.92 151.4 178.2

HOH...Formaldehydeimine (42) -6.74 -5.08 1.66 2.76 2.90 0.14 2.11 1.94 154.0 171.6

Guanidine...OHH (43) -7.96 -7.48 0.48 2.88 2.95 0.07 2.25 2.39 145.4 1