Importance of electronic delocalization on the C-N bond rotation in HCX(NH2) (X = O, NH, CH2, S, and Se)

Journal of Physical Chemistry A

Volumn 107, Issue 46, 2003, Pages 10011-10018

  Mo, Yirong ^a,b   Von Ragué Schleyer, Paul ^c   Wu, Wei ^b   Lin, Menghai ^b   Zhang, Qianer ^b   Gao, Jiali ^d  

^a WESTERN MICHIGAN UNIVERSITY   (United States)

^b XIAMEN UNIVERSITY   (China)

^c UNIVERSITY OF GEORGIA   (United States)

^d University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; CONFORMATIONS; DECOMPOSITION; ELECTRON ENERGY LEVELS; ELECTRON RESONANCE; ELECTRONIC DENSITY OF STATES; ELECTRONIC STRUCTURE; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS;

ATOMS-IN-MOLECULES THEORY; BLOCK LOCALIZED WAVE FUNCTION METHOD; CARBONYL POLARIZATION; ELECTRONEGATIVITY; ELECTRONIC DELOCALIZATION; FORMAMIDE; HYPERCONJUGATION EFFECTS;

CHEMICAL BONDS;

EID: 0345566314     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp036560c     Document Type: Article

References (78)

1. (a) Tasaki, K.; Suter, U. W. J. Phys. Chem. 1988, 92, 5886.
2. (b) Schnur, D. M.; Yuh, Y. H.; Dalton, D. R. J. Org. Chem. 1989, 54, 3779.
3. (c) Li, Y.; Garrell, R. L.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5896.
4. (d) Tsuzuki, S.; Tanabe, K. J. Chem. Soc., Perkin Trans. 2 1991, 1255.
5. (e) Duffy, E. M.; Severance, D. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1992, 114, 7535.
6. (f) Gao, J. J. Am. Chem. Soc. 1993, 115, 2930.
7. (g) Gao, J. Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 507.
8. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960.
9. (b) Wheland, G. W. Resonance in Organic Chemistry; Wiley: New York, 1955.
10. Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry; Macmillan: New York, 1992.
11. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Exford University Press: Oxford, U.K., 1990.
12. Wiberg, K. B. Acc. Chem. Res. 1999, 32, 922.
13. Wiberg, K. B.; Breneman, C. M. J. Am. Chem. Soc. 1992, 114, 831.
14. (b) Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
15. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201.
16. Knight, E. T.; Allen, L. C. J. Am. Chem. Soc. 1995, 117, 4401.
17. Laidig, K. E.; Cameron, L. M. Can. J. Chem. 1993, 71, 872.
18. Laidig, K. E.; Cameron, L. M. J. Am. Chem. Soc. 1996, 118, 1737.
19. Fogarasi, G.; Szalay, P. G. J. Phys. Chem. A 1997, 101, 1400.
20. Glengening, E. D.; Hrabal, J. A., II. J. Am. Chem. Soc. 1997, 119, 12940.
21. Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum Press: New York, 1988; p 227.
22. (b) Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.
23. Lauvergnat, D.; Hiberty, P. C. J. Am. Chem. Soc. 1977, 119, 9478.
24. Mo, Y.; Wu, W.; Zhang, Q. J. Phys. Chem. 1994, 98, 10048.
25. (b) Mo, Y.; Wu, W.; Zhang, Q. J. Mol. Struct. (THEOCHEM) 1994, 315, 173.
26. (c) Mo, Y.; Zhang, Q. Int. J. Quantum Chem. 1995, 56, 19.
27. (d) Mo, Y.; Lin, Z.; Wu, W.; Zhang, Q. J. Phys. Chem. 1996, 100, 6469.
28. (e) Mo, Y.; Lin, Z.; Wu, W.; Zhang, Q. J. Phys. Chem. 1996, 100, 11569.
29. Hiberty, P. C.; Byrman, C. P. J. Am. Chem. Soc. 1995, 117, 9875.
30. Mo, Y.; Peyerimhoff, S. D. J. Chem. Phys. 1998, 109, 1687.
31. (b) Mo, Y.; Zhang, Y.; Gao, J. J. Am. Chem. Soc. 1999, 121, 5737.
32. (c) Mo, Y.; Gao, J.; Peyerimhoff, S. D. J. Chem. Phys. 2000, 112, 5530.
33. Zhang, Q.; Li, X. J. Mol. Struct. (THEOCHEM) 1989, 198, 413.
34. (b) Li, X.; Zhang, Q. Int. J. Quantum Chem. 1989, 36, 599.
35. (c) Wu, W.; Mo, Y.; Zhang, Q. J. Mol. Struct. (THEOCHEM) 1993, 283, 227.
36. (d) Wu, W.; Wu, A.; Mo, Y.; Lin, M.; Zhang, Q. Int. J. Quantum Chem. 1998, 67, 287.
37. Cooper, D. L.; Thorsteinsson, T.; Gerratt, J. Adv. Quantum Chem. 1999, 32, 51.
38. (b) Karadakov, P. B.; Cooper, D. L.; Gerratt, J. J. Am. Chem. Soc. 1998, 120, 3975.
39. (c) Gerratt, J.; Cooper, D. L.; Karadakov, P. B.; Raimondi, M. Chem. Soc. Rev. 1997, 26, 87.
40. (d) Cooper, D. L.; Gerratt, J.; Raimondi, M. Chem. Rev. 1991, 91, 929.
41. (e) McWeeny, R. Int. J. Quantum Chem. 1988, 34, 25.
42. (f) McWeeny, R. Pure Appl. Chem. 1989, 61, 2087.
43. (g) McWeeny, R. J. Mol. Struct. (THEOCHEM) 1991, 229, 29.
44. (h) Shurki, A.; Hiberty, P. C.; Shaik, S. J. Am. Chem. Soc. 1999, 121, 822.
45. (i) Mestres, J.; Hiberty, P. C. New J. Chem. 1996, 20, 1213.
46. (j) Lauvergnat, D.; Hiberty, P. C.; Danovich, D.; Shaik, S. J. Phys. Chem. 1996, 100, 5715.
47. (k) Hiberty, P. C. J. Mol. Struct. (THEOCHEM) 1998, 451, 237.
48. Basch, H.; Hoz, S. Chem. Phys. Lett. 1998, 294, 117.
49. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structures; Wiley: New York, 1992.
50. (b) Loewenstein, A.; Melera, A.; Rigny, P.; Walter, W. J. Phys. Chem. 1964, 68, 1597.
51. (c) Neuman, R. C., Jr.; Young, L. B. J. Phys. Chem. 1965, 69, 2570.
52. (d) Sandstrom, J. J. Phys. Chem. 1967, 71, 2318.
53. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1979, 79, 517.
54. (f) Ou, M.-C.; Tsai, M.-S.; Chu, S.-Y. J. Mol. Struct. 1994, 310, 247.
55. Prasad, B. V.; Uppal, P.; Bassi, P. S. Chem. Phys. Lett. 1997, 276, 31.
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian; Gaussian, Inc.: Pittsburgh, PA, 1995.
57. (a) Mo, Y.; Lin, Z. J. Chem. Phys. 1996, 105, 1046.
58. (b) Mo, Y.; Schleyer, P.v.R.; Jiao, H.; Lin, Z. Chem. Phys. Lett. 1997, 280, 439.
59. (c) Minyaev, R. M.; Quapp, W.; Subramanian, G.; Schleyer, P. v.R.; Mo, Y. J. Comput. Chem. 1997, 18, 1792.
60. (d) Mo, Y.; Jiao, H.; Lin, Z.; Schleyer, P. v. R. Chem. Phys. Lett. 1997, 289, 383.
61. (e) Mo, Y.; Lin, M.; Wu, W.; Zhang, Q.; Schleyer, P.v. R. Sci. China 1999, 42, 253.
62. Daudey, J. P.; Trinquier, G.; Barthelat, J. C.; Malrieu, J. P. Tetrahedron 1980, 36, 3399.
63. (b) Mo, Y.; Lin, M.; Wu, W.; Zhang, Q. Acta Chim. Sin. 2000, 58, 218.
64. Felgg, R. H.; Harcourt, R. D. J. Mol. Struct. (THEOCHEM) 1988, 164, 67.
65. Glendening, E. D.; Badenhoop, J. K.; Weinhold, F. J. Comput. Chem. 1998, 19, 628.
66. Hiberty, P. C.; Ohanessian, G. J. Am. Chem. Soc. 1982, 104, 66.
67. Schleyer, P.v. R.; Kos, A. J. Tetrahedron 1983, 39, 1141
68. (b) Jemmis, E. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1982, 104, 4781.
69. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1987, 109, 7362.
70. (d) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
71. (e) Farnham, W. B.; Smart, B. E.; Middleton, W. J.; Calabrese, J. C.; Dixon, D. A. J. Am. Chem. Soc. 1985, 107, 4565.
72. (f) Reed, A. E.; Schade, C.; Schleyer, P. v. R.; Kamath, P. V.; Chandrasekhar, J. J. Chem. Soc., Chem. Commun. 1988, 67.
73. (g) Salzner, U.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1990, 190.
74. (h) Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1993, 115, 614.
75. Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 14, 1504.
76. Wiberg, K. B.; Hadad, C. M., Breneman, C. M.; Laigig, K. E.; Murcko, M. A.; LePage, T. J. Science 1991, 252, 1266.
77. Mo, Y.; Peyerimhoff, S. D. Theor. Chem. Acc. 1999, 101, 311.
78. Reed, A. E.; Weinhold, F.; Curtiss, L. A. Chem. Rev. 1988, 88, 899.