Remarkable thiocarbonyl and ring-size effects on the amide bond twisting

Chemistry Letters

Volumn , Issue 8, 2001, Pages 750-751

  Yamada, Shinji ^a   Matsuda, Kaori ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035538643     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.750     Document Type: Article

References (18)

1. M. B. Robin, F. A. Bovey, and H. Basch in "The Chemistry of Amides," ed. by J. Zabicky, Wiley-Interscience, London (1970), p 1.
2. S. Yamada in "The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science," ed. by A. Greenberg, C. M. Breneman, and J. F. Liebman, John Wiley & Sons, Inc., New York (2000), Chap. 8, p 215.
3. For examples see, a) L. T. Tan, R. T. Williamson, and W. H. Gerwick, J. Org. Chem., 65, 419 (2000).
4. b) N. Xi, L. B. Alemany, and M. A. Ciufolini, J. Am. Chem. Soc., 120, 80 (1998).
5. c) Y. Endo, M. Ohno, M. Hirano, A. Itai, and K. Shudo, J. Am. Chem. Soc., 118, 1841 (1996).
6. d) M. K. Rosen, B. F. Standaert, A. Galat, M. Nakatsuka, and S. L. Schreiber, Science, 248, 863 (1990).
7. S. Yamada, Angew. Chem., Int. Ed. Engl., 32, 1083 (1993).
8. S. Yamada, N. Nunami, and K. Hori, Chem. Lett., 1998, 451.
9. H. R. Bravo and B. E. Weiss-Lopez, Bol. Soc. Chil. Quim., 44, 443 (1999).
10. W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reibig, and V. Voerckel, Chem. Ber., 125, 2719 (1992).
11. M. Mazaruddin and G. Thyagarajan, Tetrahedron, 25, 517 (1969).
12. S. Yamada, J. Org. Chem., 61, 941 (1996).
13. 2 = 0.1558.
14. For definitions of τ, see: F. K. Winkler and J. D. Dunitz, J. Mol. Biol., 59, 169 (1971) and ref 4.
15. C. N. Cow, J. F. Britten, and P. H. M. Harrison, Chem. Commun., 1998, 1147.
16. Y. Nagao, T. Ikeda, T. Inoue, M. Yagi, M. Shiro, and E. Fujita, J. Org. Chem., 50, 4072 (1985).
17. The RHF/3-21G * calculations were performed by using PC Spartan pro. The twist angles are as follows: 1: 21.6°; 2: 69.3° 3: 15.7°.
18. A. J. Kirby, I. V. Komarov, K. Kowski, and P. Rademacher, J. Chem. Soc., Perkin Trans. 2, 1999, 1313.