C(sp2)-C(sp3) Rotational Barriers in Simple Amides: H2N-C(=O)-R (R = Methyl, Ethyl, i-Propyl, terf-Butyl)

Journal of Physical Chemistry A

Volumn 103, Issue 7, 1999, Pages 893-902

  Sandrone, Giovanni ^a   Dixon, David A ^a   Hay, Benjamin P ^a  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001552802     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp982649k     Document Type: Article

References (75)

1. Zabicky, J. The Chemistry of Amides: Wiley-Interscience: New York, 1970.
2. Sigel, H.; Martin, R. B. Chem. Rev. 1982, 82, 385.
3. Clement, O.; Rapko, B. M.; Hay, B. P. Coord. Chem. Rev. 1998, 170, 203.
4. (a) Cuillerdier, C.; Musikas, C.; Hoel, P.; Nigond, L.; Vitart, X. Sep. Sci. Technol. 1991, 26, 1229.
5. (b) Ruikar, P. B.; Nagar, M. S.; Pai, S. A.; Subramanian, M. S. J. Radioanal. Nucl. Chem. 1991, 150, 473.
6. (c) Condamines, N.; Musikas, C. Solv. Extr. Ion Exch. 1992, 10, 69.
7. (d) Prabhu, D. R.; Mahajan, G. R.; Nair, G. M.; Subramanian, M. S. Radiochim. Acta 1993, 60, 109.
8. (e) Nair, G. M.; Prabhu, D. R.; Mahajan, G. H.; Shukla, J. P. Solv. Extr. Ion Exch. 1993, 11, 831.
9. (f) Cuillerdier, C.; Musikas, C.; Nigond, L. Sep. Sci. Technol. 1993, 28, 155.
10. (g) Tian, Q.; Hughes, M. A. Hydrometallurgy 1994, 36, 79.
11. (h) Borong, B.; Chaohong, S.; Yizhi, B.; Gaodong, W.; Jun, Q.; Zhengbai, C. J. Radioanal. Nucl. Chem. 1994, 178, 99.
12. Nigond, L.; Musikas, C.; Cuillerdier, C. Solv. Extr. Ion Exch. 1994, 12, 297.
13. (j) Nakamura, T.; Miyake, C. Solv. Extr. Ion Exch. 1995, 13, 253.
14. (k) Nair, G. M.; Mahajan, G. R.; Prabhu, D. R. J. Radioanal. Nucl. Chem. 1995, 191, 323.
15. (l) Nigond, L.; Coudamines, N.; Cordier, P. Y.; Livet, J.; Madic, C.; Cuillerdier, C.; Musikas, C. Sep. Sci. Technol. 1995, 30, 2075.
16. (m) Ruikar, P. B.; Nagar, M. S.; Subramanian, M. S.; Gupta, K. K.; Varadarajan, N.; Singh, R. K. J. Radioanal. Nucl. Chem., Lett. 1995, 201, 125.
17. (n) Wang, Y.-S.; Sun, G.-X.; Xie, D.-F.; Bao, B.-R.; Cao, W.-G. J. Radioanal. Nucl. Chem., Lett. 1996, 214, 67.
18. (o) Wang, Y.-S.; Shen, C.-H.; Yang, Y.-H.; Zhu, J.-K.; Bao, B.-R. J. Radioanal. Nucl. Chem., Lett. 1996, 213, 199.
19. (p) Shen, C.; Bao, B.; Zhu, J.; Wang, Y.; Cao, Z. J. Radioanal. Nucl. Chem., Lett. 1996, 212, 187.
20. (q) Beer, P.; Drew, M. G. B.; Grieve, A.; Kan, M.; Leeson, P. B.; Nicholson, G.; Ogden, M. I.; Williams, G. J. Chem. Soc., Chem. Commun. 1996, 1117.
21. (r) Sasaki, Y.; Choppin, G. J. Radioanal. Nucl. Chem. 1996, 207, 383.
22. (s) Chan, G. Y. S.; Drew, M. G. B.; Hudson, M. J.; Iveson, P. B.; Lijenzin, J.-O.; Skalberg, M.; Spjuth, L.; Madic, C. J. Chem. Soc., Dalton Trans. 1997, 649.
23. (a) Konings, M. S.; Dow, W. C.; Love, D. B.; Raymond, K. N.; Quay, S. C.; Rocklage, S. M. Inorg. Chem. 1990, 29, 1488.
24. (b) Aime, S.; Anelli, P. L.; Botta, M.; Fedeli, F.; Grandi, M.; Paoli, P.; Uggeri, F. Inorg. Chem. 1992, 31, 2422.
25. (c) Morrow, J. R.; Amin, S.; Lake, C. H.; Churchill, M. R. Inorg. Chem. 1993, 32, 4566.
26. (d) Geze, C.; Mouro, C.; Hindre, F.; Le Plouzennec, M.; Moinet, C.; Rolland, R.; Alderighi, L.; Vacca, A.; Simonneaux, G. Bull. Soc. Chim. Fr. 1996, 133, 267.
27. Hay, B. P.; Clement, O.; Sandrone, G.; Dixon, D. A. Inorg. Chem. 1998, 37, 5887.
28. McCanunon, J. A.; Harvey, S. C. Dynamics of Proteins and Nucleic Acids; Cambridge University Press: Cambridge, UK, 1987.
29. Bohm, H.; Brode, S. J. Am. Chem. Soc. 1991, 113, 7129.
30. Tanabe, K.; Osawa, E.; Tsuzuki, S.; Uchimaru, T. Chem. Express 1987, 2, 329.
31. Schnur, D. M.; Yuh, Y. H.; Dalton, D. R. J. Org. Chem. 1989, 54, 3779.
32. Lii, J.-H.; Gallion, S.; Bender, C.; Wikstrom, H.; Allinger, N. L.; Flurchick, K. M.; Teeter, M. M. J. Camput. Chem. 1989, 10, 503.
33. Lii, J.-H.; Allinger, N. L. J. Comput. Chem. 1991, 12, 186.
34. Maple, J. R.; Hwang, M.-J.; Jalkanen, K. J.; Stockfish, T. P.; Hagler, A. T. J. Comput. Chem. 1997, 19, 430.
35. Hagler, A. T.; Leiserowitz, L.; Tuval, M. J. Am. Chem. Soc. 1976, 98, 8, 4600.
36. Filiaux, F.; Thomkinson, J. Chem. Phys. 1977, 26, 295.
37. Kojima, T.; Yano, E.; Nakagawa, K.; Tsunekawa, S. J. Mol. Spectrosc. 1985, 1985, 494.
38. Jeffrey, G. A.; Ruble, J. R.; McMullan, R. K.; DeFrees, D. J.; Binkley, J. S.; Pople, J. A. Acta Crystallogr., Sect. B 1980, 36, 2292.
39. Radom, L.; Lathan, W. A.; Herhe, W. J.; Pople, J. A. Aust. J. Chem. 1972, 25, 1601.
40. Sugawara, Y.; Hirakawa, A. Y.; Tsuboi, M.; Kato, S.; Morokuma, K. J. Mol. Spectrosc. 1986, 115, 21.
41. Tasaki, K.; Suter, U. W. J. Phys. Chem. 1988, 92, 5886.
42. Gaussian 94; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; 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. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
43. (a) Andzelm, J.; Wimmer, E.; Salahub, D. R. In The Challenge of d and f Electrons: Theory and Computation; Salahub, D. R., Zerner, M. C., Eds.; ACS Symposium Series, No. 394; American Chemical Society: Washington, DC, 1989; p 228.
44. (b) Andzelm, J. In Density Functional Theory in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer-Verlag: New York, 1991; p 155.
45. Andzelm, J. W.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280. DGauss is a density functional program which is part of Unichem and is available from Oxford Molecular.
46. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
47. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1.
48. Dunning, T. H., Jr.; Hay, P. J. Methods of Electronic Structure Theory; Plenum Press: New York, 1977.
49. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules. Oxford University Press: New York, 1989;
50. (b) Labanowski. J.; Andzelm, J., Eds. Density Functional Methods in Chemistry. Springer-Verlag: New York, 1991.
51. (c) Ziegler, T. Chem. Ret: 1991, 91, 651.
52. (d) Salahub, D. R. In Ab Initio Methods in Quantum Chemistry - II: Lawley, K. P., Ed.; J. Wiley & Sons: New York, 1987; p 447.
53. (e) Jones, R. O.; Gunnarsson, O. Rev. Mod. Phys. 1989, 61, 689.
54. Vosko, S. J.; Wilk, L.; Nusair, W. Can. J. Phys. 1980, 58, 1200.
55. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
56. (b) Becke, A. D. In The Challenge of d and f Electrons: Theory and Computation; Salahub, D. R., Zerner, M. C., Eds.; ACS Symposium Series. No. 394; American Chemical Society: Washington, DC, 1989; p 166.
57. Becke, A. D. Int. J. Quantum Chem. Symp. 1989, 23, 599.
58. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
59. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
60. MM3(96). The program may be obtained from Tripos Associates, 1699 S. Hanley Road, St. Louis, MO 63144, for commercial users, and it may be obtained from the Quantum Chemistry Program Exchange, Mr. Richard Counts, QCPE, Indiana University, Bloomington, IN 47405, for noncommercial users.
61. Allinger, N. L.; Chen, K.; Rahman, M.; Pathiaseril, A. J. Am. Chem. Soc. 1991, 113, 4505.
62. Wong, M. W.; Wiberg, K. B. J. Phys. Chem. 1992, 96, 668.
63. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
64. (b) Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
65. (c) Woon, D. E.; Dunning T. H., Jr. J. Chem. Phys. 1993, 99, 1914.
66. (d) Peterson, K. A.; Kendall, R. A.; Dunning T. H., Jr. J. Chem. Phys. 1993, 99, 1930.
67. (e) Peterson, K. A.; Kendall, R. A.; Dunning, T. H. Jr. J. Chem. Phys. 1993, 99, 9790.
68. (f) Woon, D. E.; Dunning T. H., Jr. J. Chem. Phys. 1995, 103, 4572.
69. Kitano, M.; Kuchitsu, K. Bull. Chem. Soc. Jpn 1973, 46, 3081.
70. Ma, B.; Lii, J.-H.; Schaefer, H. F.; Allinger, N. L. J. Phys. Chem. 1996, 100, 8763.
71. Usanmaz, A.; Adler, G. Acta Crystallogr., Sect. B 1982, 38, 660.
72. Allen, F. H.; Bellard, S. A.; Brice, B. A.; Cartwright, A.; Doubleday: A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G., Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. Acta Crystallogr., Section B 1979, 35, 2331.
73. Cohen-Addad, C.; Cohen-Addad, J.-P. J. Chem. Soc., Perkin Trans. 2 1978, 168.
74. Cohen-Addad, C.; Grand, A. Acta Crystallogr., Sect. B 1974, 30, 1342.
75. Andreetti, G. D.; Bocelli, G.; Cybulski, J.; Dabrowski, Z.; Wrobel, J. T. J. Mol. Struct. 1985, 128, 259.