Probing the influence of solvent effects on the conformational behavior of 1,3-diazacyclohexane systems

Journal of Physical Chemistry A

Volumn 111, Issue 39, 2007, Pages 9884-9889

  Singh, Ajeet ^a   Ganguly, Bishwajit ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CONFORMATIONS; HYDROGEN BONDS; STABILITY;

ANOMERIC STABILIZATIONS; CONTINUUM MODELS; HYPERCONJUGATIVE STABILIZATIONS; STRUCTURAL PARAMETERS;

AROMATIC COMPOUNDS;

EID: 35348974503     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp074146x     Document Type: Article

References (71)

1. (a) The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Symposium Series No. 539; American Chemical Society: Washington, DC, 1993.
2. (b) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
3. (c) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer: Berlin, 1983.
4. (d) Anomeric Effect. Origins and Consequences; Szarek, W. A., Horton, D., Eds.; ACS Symposia Series No. 87; American Chemical Society: Washington, DC, 1979.
5. (e) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Wiley: New York, 1983.
6. (f) Lemieux, R. U. Pure Appl. Chem. 1971, 25, 527.
7. (g) Romers, C.; Altona, C.; Buys, H. R.; Havinga, E. Top. Stereochem. 1969, 4, 39.
8. (h) Jeffrey, G. A.; Pople, J. A.; Binkley, J. S.; Vishveshwara, S. J. Am. Chem. Soc. 1978, 100, 373.
9. (i) Smits, G. F.; Krol, M. C.; Altona, C. Mol. Phys. 1988, 65, 513.
10. (j) Lemieux, R. U. In Molecular Rearrangements; De Mayo, P., Ed.; Interscience Publishers: New York, 1964; p 709.
11. (a) Altona, C. Ph.D. Thesis, University of Leiden, 1964.
12. (b) David, S.; Eisenstein, O.; Hehre, W. J.; Salem, L.; Hoffmann, R. J. Am. Chem. Soc. 1973, 95, 3806.
13. (a) Reed, A. E.; Schleyer, P. v. R. Inorg. Chem. 1988, 27, 3969.
14. (b) Salzner, U.; Schleyer, P. v. R. J. Org. Chem. 1994, 59, 2138 and references cited therein.
15. (a) Schleifer, L.; Senderowitz, H.; Aped, P.; Tartakovsky, E.; Fuchs, B. Carbohydr. Res. 1990, 206, 21.
16. (b) Fuchs, B.; Schleifer, L.; Tartakovsky, E. Nouv. J. Chim. 1984, 8, 275.
17. (c) Fuchs, B.; Ellencweig, A.; Tartakovsky, E.; Aped, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 287.
18. (d) Aped, P.; Apeloig, Y.; Ellencweig, A.; Fuchs, B.; Goldberg, I.; Karni', M.; Tartakovsky, E. J. Am. Chem. Soc. 1987, 109, 1486.
19. (e) Aped, P.; Fuchs, B.; Schleifer, L.; Wolfe, S. J. Comput. Chem. 1989, 10, 265.
20. (f) Senderowitz, H.; Aped, P.; Fuchs, B. Helv. Chim. Acta 1990, 73, 2113.
21. (g) Senderowitz, H.; Aped, P.; Fuchs, B. J. Comput. Chem. 1993, 14, 944.
22. (h) Senderowitz, H.; Aped, P.; Fuchs, B. Tetrahedron 1993, 49, 3879.
23. (i) Senderowitz, H.; Fuchs, B. J. Mol. Struct. (THEOCHEM) 1997, 395, 123.
24. (j) Reany, O.; Goldberg, I.; Abramson, S.; Golender, L.; Ganguly, B.; Fuchs, B. J. Org. Chem. 1998, 63, 8850.
25. (k) Kleinpeter, E.; Taddei, F.; Wacker, P. Chem. Euro. J. 2003, 9, 1360.
26. (l) Alabugin, I. V. J. Org. Chem. 2000, 65, 3910.
27. Van der Does, H.; Mijlhoff, F. C.; Reres, G. H. J. Mol. Struct. 1981, 74, 153.
28. (a) Riddel, F. G.; Williams. F. G. Tetrahedron Lett. 1971, 2073.
29. (b) Blackbume, I. D.; Katritzky, A. R.; Read, D. M.; Chivers, P. J.; Crabb, T. A. J. Chem. Soc., Perkin Trans. II 1976, 418.
30. (c) Chive, P. J.; Crabb, T. A. Tetrahedron 1970, 26, 3369.
31. (d) Katritzky, A. R.; Brito-Palma, F. M. S.; Baker, V. J. J. Chem. Soc., Perkin Trans. II 1980, 1739.
32. (e) Katritzky, A. R.; Baker, V. J.; Brito-Palma, F. M. S.; Ferguson, I.; Angiolini, J. L. J. Chem. Soc., Perkin Trans. II 1980, 1746.
33. (f) Jones, R. A. Y.; Katritzsky, A. R.; Snarey. M. J. Chem. Soc. B 1970, 131.
34. (g) Katritzsky, A. R.; Baker, V. J.; Ferguson, I. J.; Pate, R. C. J. Chem. Soc., Perkin Trans. II 1979, 143.
35. (h) Armarego, W. L. F.; Jones. R. A. Y.; Katritzsky, A. R.; Read, D. M.; Scattergood, R. Aust. J. Chem. 1975, 28, 2323.
36. (i) Armarego, W. L. F.; Kobayishi, T. J. Chem. Soc. C 1971, 1912.
37. (a) Crabb, T. A.;. Katritzky, A. R. Adv. Heterocycl. Chem. 1983, 36, 1 and references cited therein.
38. (b) Kleinpeter, E. Adv. Heterocycl. Chem. 2004, 66, 42.
39. (a) Salzner, U. J. Org. Chem. 1995, 60, 986.
40. (b) Locke, J. M.; Crumbie, R. L.; Griffith, R.; Bailey, T. D.; Boyd, S.; Roberts, J. D. J. Org. Chem. 2007, 72, 4156.
41. (a) Kagabu, S.; Hibi, M.; Nishimura, K. Biosci. Biotechnol. Biochem. 2005, 69, 705.
42. (b) Axenrod, T.; Sun, J.; Das, K. K.; Dave, P. R.; Forohar, F.; Kaselji, M.; Trivedi, N. J.; Gilardi, R. D.; Flippen-Andersen, J. L. J. Org. Chem. 2000, 65, 1200.
43. Jaguar, 5.5 ed.; Schrodinger, Inc.: Portland, OR, 2004.
44. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
45. Lee, C. T.; Wang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
46. (a) Brunck, T. K.; Weinhold, F. J. Am. Chem. Soc. 1978, 102, 1700.
47. (b) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
48. (c) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
49. (d) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
50. (e) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
51. (f) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
52. (a) Salzner, U.; Schleyer, P. v. R. J. Am. Chem. Soc. 1993, 115, 10231.
53. (b) Carballeira, L.; Perez-Juste, I. J. Org. Chem. 1997, 62, 6144.
54. Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A., III; Honig, B. J. Am. Chem. Soc. 1994, 116, 11875.
55. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775.
56. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
57. (a) Perrin, C. L.; Young, D. B. Tetrahedron Lett. 1995, 36, 7185.
58. (b) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715.
59. (c) Wiberg, K. B.; Murcko, M. A. J. Chem. Phys. 1987, 91, 3616.
60. 13e,f
61. (a) Cramer, C. J. J. Org. Chem. 1992, 57, 7034.
62. (b) Montagnani, R.; Tomais, J. Int. J. Quantum Chem. 1991, 39, 851.
63. (a) Carballeira, L.; Perez-Juste, I. J. Org. Chem. 1997, 62, 6144.
64. (b) Carballeira, L.; Perez-Juste, I. J. Comput. Chem. 2000, 21, 462.
65. Alagona, G.; Ghio, C. J. Mol. Struct. (THEOCHEM) 1992, 254, 287.
66. (a) Hu, C.-H.; Shen, M.; Schaefer, H. F., III. J. Am. Chem. Soc. 1993, 115, 2923.
67. (b) Barone, V.; Adamo, C.; Lelji, F. J. Chem. Phys. 1995, 102, 364.
68. (a) Doo-Sik, A.; Lee, S.; Cheong, W. J. Bull. Kor. Chem. Soc. 2004, 25, 1161.
69. (b) Cringus, D.; Yeremenko, S.; Pshenichnikov, M. S.; Wiersma, D. A. J. Phys. Chem. B 2004, 108, 10376.
70. (c) Chaudhari, A.; Lee, S.-L. Int. J. Quantum Chem. 2005, 102, 106.
71. (d) Kryachko, E. S.; Nguyen, M. T. J. Phys. Chem. A 2002, 106, 4267.