Gauche effect in 1,2-difluoroethane. Hyperconjugation, bent bonds, steric repulsion

Journal of Physical Chemistry A

Volumn 109, Issue 6, 2005, Pages 1223-1229

  Goodman, Lionel ^a   Gu, Hongbing ^a   Pophristic, Vojislava ^a,b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF THE SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENT BONDS; GAUCHE EFFECTS; HYPERCONJUGATION; STERIC REPULSION;

ANGLE MEASUREMENT; CHARGE TRANSFER; CHEMICAL BONDS; ELECTROCHEMISTRY; ELECTRON ENERGY LEVELS; ELECTROSTATICS; FLUORINE; HYDRAZINE; MOLECULAR DYNAMICS; STABILIZATION;

ETHANE;

EID: 14544303540     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp046290d     Document Type: Article

References (41)

1. Wolfe, S. Acc. Chem. Res. 1972, 5 (3), 102-111.
2. Durig, J. R.; Liu, J.; Little, T. S.; Kalasinsky, V. F. J. Phys. Chem. 1992, 96 (21), 8224-8233.
3. Craig, N. C.; Chen, A.; Suh, K. H.; Klee, S.; Mellau, G. C.; Winnewisser, B. P.; Winnewisser, M. J. Phys. Chem. A 1997, 101 (49), 9302-9308.
4. Fernholt, L.; Kveseth, K. Acta Chem. Scand., A: Phys. Inorg. Chem. 1980, A34 (3), 163-170.
5. Takeo, Harutoshi; Matsumura, Chi; Morino, Yonezo. J. Chem. Phys. 1986, 84 (8), 4205-4210.
6. Goodwin, A. R. H.; Morrison, G. J. Phys. Chem. 1992, 96 (13), 5521-5526.
7. Radom, L.; Lathan, W. A.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1973, 95, 693-698.
8. Brunck, T. K.; Weinhold, F. J. Am. Chem. Soc. 1979, 101 (7), 1700-1709.
9. Rablen, P. R.; Hoffmann, R. W.; Hrovat, D. A.; Borden, W. T. J. Chem. Soc., Perkin Trans. 2: 1999, No. 8, 1719-1726.
10. Wiberg, K. B.; Murcko, M. A.; Laidig, K. E.; MacDougall, P. J. J. Phys. Chem. 1990, 94 (18), 6956-6959.
11. Wiberg, K. B. Acct. Chem. Res. 1996, 29 (5), 229-234.
12. Trindle, C.; Crum, P.; Douglass, K. J. Phys. Chem. A 2003, 107 (32), 6236-6242.
13. Box, Vernon G. S.; Box, Lynda L. J. Mol. Struct. 2003, 649 (1-2), 117-132.
14. Chen, K.-H.; Walker, G. A.; Allinger, N. L. THEOCHEM 1999, 490, 87-107.
15. Engkvist, O.; Karlstroem, G.; Widmark, P.-O. Chem. Phys. Lett. 1997, 265 (1, 2), 19-23.
16. Papasavva, Stella; Illinger, Karl H.; Kenny, Jonathan E. J. Phys. Chem. 1996, 100 (24), 10100-10110.
17. Martell, J. M.; Boyd, R. J.; Shi, Z. J. Phys. Chem. 1993, 97 (28), 7208-7215.
18. Topol, I. A.; Burt, S. K. Chem. Phys. Lett. 1993, 204 (5-6), 611-616.
19. Dixon, D. A.; Matsuzawa, N.; Walker, S. C. J. Phys. Chem. 1992, 96 (26), 10740-10746.
20. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1988, 92 (10), 2729-2733.
21. Wiberg, K. B.; Murcko, M. A. J. Phys. Chem. 1987, 91 (13), 3616-3620.
22. Miyajima, Takashi; Kurita, Yasuyuki; Hirano, Tsuneo. J. Phys. Chem. 1987, 91 (15), 3954-3959.
23. Smits, G. F.; Krol, M. C.; Van Kampen, P. N.; Altona, Cs. THEOCHEM 1986, 32 (3-4), 247-253.
24. Radom, L.; Baker, I.; Gill, P. M. W.; Nobes, R. H.; Riggs, N. V. J. Mol. Struct. 1985, 126, 271-290.
25. Wetpetinski, K. S.; Cook, M. J. Chem. Phys. 1997, 106 (17), 7124-7138.
26. Wolfe, S.; Rank, A.; Tel, L. M.; Csizmadia, I. G. J. Chem. Soc. B: Phys. Org. 1971, 1, 136-145.
27. Weinhold, F. In The Encyclopedia of Computational Chemistry; P. v. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. A. Kollman, H. F. Schaefer III, P. R. Schreiner, Eds.; John Wiley & Sons: Chichester, U.K., 1998; pp 1792-1811.
28. Frisch, M. J.; Trucks, G. H.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, I.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
29. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.0 and NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, 1996 and 2002.
30. Weisskopf, V. F. Science 1975, 187, 605-612.
31. Badenhoop, J. K.; Weinhold, F. J. Chem. Phys. 1997, 107 (14), 5406-5421, 5422.
32. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83 (4), 1736-1740.
33. Runtz, G. R.; Bader, R. F. W.; Messer, R. R. Canad. J. Chem. 1977, 55 (16), 3040-3045.
34. Pophristic, V.; Goodman, L. Nature 2001, 411 (6837), 565-568.
35. Pophristic, V.; Goodman, L. J. Phys. Chem. A 2003, 107, 3538.
36. Pophristic, V.; Goodman, L.; Gorb, L.; Leszczynski, J. J. Chem. Phys. 2002, 116, 7049.
37. Pophristic, V.; Goodman, L. J. Phys. Chem. 2002, 106 (8), 1642-1646.
38. Wilcox, C. F.; Bauer, S. H. J. Mol. Struct. (THEOCHEM), 2003, 625, 1-8.
39. Wolfe, S.; Shi, Z. Isr. J. Chem. 2000, 40 (3-4), 343-355.
40. 41 to aromatic aldehydes and complex sugars.
41. Goodman, L.; Sauers, R. Unpublished work.