II
Lii and Allinger
2
Table S-1. Binding Energies and Geometries for Ethylene-Ammonia Complex
I. C2H4-NH3, Cs (1) (C=C is htdrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -1.84
BSSE -1.09
E(corrected) -0.75 -0.76 -0.78 Dipole Moment 1.981 1.511 1.500 Imaginary Fre. 1 NA 1 C=C...N dist. 3.715 3.687 3.723 C=C...H dist. 2.734 3.153 2.710 N-H bond length 1.012 1.015 1.015 <(C=)C...N-H 12.1 51.2 2.9
II. C2H4-NH3, C1 (2) (C=C is htdrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -1.75
BSSE -1.01
3
Table S-2. Binding Energies and Geometries for Ethylene-Acethylene Complex
I. C2H4-C2H2, T-Shape (3) (C
=C is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -2.24
BSSE -1.14
4
Table S-3. Binding Energies and Geometries for Water-Acetylene Complex
I. H2O-C2H2, Cs (4) (O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -4.52
BSSE -2.07
E(corrected) -2.45 -0.82 -2.48 Dipole Moment 2.424 2.036 2.037 Imaginary Fre. 0 2 0 O...C+C.dist. 3.254 3.747 3.262 O...H-C+C.dist. 2.195 2.666 2.178 C-H bond length 1.067 1.081 1.084 <O...C-H 5.9 0.0 0.0
II. C2H2-H2O, Cs (5) (C
+C is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -3.11
BSSE -1.51
5
Table S-4. Binding Energies and Geometries for Ammonia-Acetylene Complex
I. NH3-C2H2, C3v (6) (N is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -5.25
BSSE -1.45
E(corrected) -3.80 -0.83 -3.79 Dipole Moment 2.726 1.496 1.504 Imaginary Fre. 0 0 0 N...C+C dist. 3.291 3.781 3.293 N...H-C+C dist. 2.218 2.700 2.206 C-H bond length 1.072 1.081 1.087 <N...C-H 0.0 0.0 0.0
II. C2H2-NH3, Cs (7) (C
+C is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -1.79
BSSE -1.06
6
Table S-5. Binding Energies and Geometries for Formaldehyde-Acethylene
Complex
I. CH2O-C2H2, C2v (8) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -3.05
BSSE -1.14
E(corrected) -1.91 -0.60 -2.01 Dipole Moment 3.510 2.485 2.480 Imaginary Fre. 1 2 2 C=O...C dist. 3.292 3.854 3.293 C=O...H dist. 2.228 2.773 2.209 C-H bond length 1.064 1.081 1.084 <(C=)O...C-H 0.0 0.0 0.0
II. CH2O-C2H2, Cyclic (9) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -4.12
BSSE -1.99
7
Table S-6. Binding Energies and Geometries for Acetylene Dimer
I. C2H2-C2H2, T-Shape (10) (Acetylene is both hydrogen donor and acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -2.14
BSSE -1.12
8
Table S-7. Binding Energies and Geometries for Formamide-Water Complex
I. HCONH2-H2O, Cyclic (11) (both C=O and O are hydrogen acceptors)
MP2/6-31g** MM3 MM3(96) E(binding) -12.92
BSSE -4.47
E(corrected) -8.45 -8.85 -8.47 Dipole Moment 3.570 2.727 1.634 Imaginary Fre. 0 0 0 C=O...O dist. 2.829 2.830 2.822 C=O...H dist. 1.936 2.093 1.982 N...O-H dist. 2.875 2.981 2.887 N-H...O-H dist. 2.018 2.168 2.021 O-H bond length 0.974 0.949 0.954 <C=O...O(-H) 96.2 98.6 96.7 <C-N...O(-H) 91.4 88.3 90.2 <C=O...H(-O) 105.5 107.7
II. HCONH2-H2O, C1 (12) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -8.68
BSSE -3.66
9
Table S-8. Binding Energies and Geometries for Formamide-Methanol Complex
I. HCONH2-CH3OH, Cyclic (13) (both C=O and O are hydrogen acceptors)
MP2/6-31g** MM3 MM3(96) E(binding) -13.44
BSSE -4.93
E(corrected) -8.51 -9.16 -8.43 Dipole Moment 3.704 2.517 2.501 Imaginary Fre. 0 0 0 C=O...O dist. 2.805 2.853 2.795 C=O...H dist. 1.913 2.092 1.971 N...O-H dist. 2.857 3.011 2.894 N-H...O-H dist. 2.004 2.179 2.037 O-H bond length 0.975 0.949 0.955 <C=O...O(-H) 96.2 99.4 97.4 <C-N...O(-H) 91.2 88.6 89.4 <C=O...H(-O) 105.4 112.4 109.1
II. HCONH2-CH3OH, C1 (14) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -9.21
BSSE -3.99
10
Table S-9. Binding Energies and Geometries for Formamide-Formaldehyde
Complex
I. CH2O-HCONH2, Cyclic (15) (N is hydrogen donnor)
MP2/6-31g** MM3 MM3(96) E(binding) -9.88
BSSE -3.51
E(corrected) -6.37 -7.27 -6.37 Dipole Moment 1.316 1.469 1.448 Imaginary Fre. 0 1 1 C=O...N dist. 2.991 2.959 3.010 C=O...H-N dist. 1.996 1.939 1.981 O=C...O=C dist. 3.231 3.584 3.632 C-H...O=C dist. 2.276 2.774 2.802 N-H bond length 1.014 1.029 1.035 <(C=)O...N-C 110.8 112.8 113.5 <(O=)C...O=C 104.3 101.5 101.2 <C=O...H(-N) 106.8 118.2 116.2
II. CH2O-HCONH2, C1 (16) (N is hydrogen donnor)
MP2/6-31g** MM3 MM3(96) E(binding) -6.24
BSSE -2.47
11
Table S-10. Dimerization Energies and Geometries for Formamide Dimer
I. HCONH2-HCONH2, Cyclic (17) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -17.37
BSSE -4.01
12
Table S-11. Binding Energies and Geometries for Guanidinium Ion-Water
Complex
I. (NH2)3C(+)-H2O, Bifurcated (18) (H2O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -21.57
BSSE -2.20
13
Table S-12. Binding Energies and Geometries for Formate Ion-Water Complex
I. HCOO(-)-H2O, Bifurcated (19) (COO(-) is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -25.71
BSSE -6.06
14
Table S-13. Binding Energies and Geometries for Ammonium Ion-Water Complex
I. NH4(+)-H2O, Linear (20) (H2O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -24.33
BSSE -1.04
E(corrected) -23.28 -14.06 -22.63 Dipole Moment 2.668 2.160 2.155 Imaginary Fre. 0 2 0 N(+)...O dist. 2.673 2.718 2.668 N(+)-H...O dist 1.614 1.732 1.616 N-H bond length 1.059 1.050 1.052 <H-N...O 0.0 0.0 0.0
II. NH4(+)-H2O, Bifurcated (21) (H2O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -19.98
BSSE -1.06
15
Table S-14. Binding Energies and Geometries for Acetaldehyde-Methanol
Complex
I. C2H5O-CH3OH, C1 (39) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -8.52
BSSE -4.08
E(corrected) -4.44 -5.56 -4.46 Dipole Moment 3.607 3.029 3.449 Imaginary Fre. 0 NA 1 C=O...O dist. 2.903 2.958 2.918 C=O...H dist. 1.975 2.058 1.976 C...O-H dist. 3.318 3.881 3.987 C-H...O-H dist. 2.407 3.169 3.223 O-H bond length 0.969 0.949 0.953 <(C=)O...O-H 13.8 15.2 7.1 <H-C...O(-H) 27.4 43.5 40.3
II. C2H5O-CH3OH, Cs (40) (C=O is hydrogen acceptor)
MP2/6-31g** MM3 MM3(96) E(binding) -4.54
BSSE -2.44
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