Rotational barriers of 2-acetylthiophene and related carbonyl compounds

Journal of Molecular Structure: THEOCHEM

Volumn 364, Issue 2-3, 1996, Pages 131-138

  Miyahara, Yuji ^a   Inazu, Takahiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

AM1; Conformation; Gaussian 92; MM3; PM3; SAM1; Thiophene 2 carbonyl

Indexed keywords

EID: 0011945529     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-1280(95)04470-1     Document Type: Article

References (32)

1. For reviews, see: V.N. Sheinker, A.D. Garnovskii and O.A. Osipov, Russian Chem. Rev., 50 (1981) 336 (Uspekhi Khim., 50 (1981) 632). A. Kucsman, and I. Kapovits, in F. Bernadi, I.G. Csizmadia and G. Mangini (Eds.), Organic Sulfur Chemistry: Theoretical and Experimental Advances, Elsevier, Amsterdam, 1985, p. 191. R. Benassi, U. Folli, L. Schenetti and F. Taddei, Adv. Heterocycl. Chem., 41 (1987) 75.
2. For reviews, see: V.N. Sheinker, A.D. Garnovskii and O.A. Osipov, Russian Chem. Rev., 50 (1981) 336 (Uspekhi Khim., 50 (1981) 632). A. Kucsman, and I. Kapovits, in F. Bernadi, I.G. Csizmadia and G. Mangini (Eds.), Organic Sulfur Chemistry: Theoretical and Experimental Advances, Elsevier, Amsterdam, 1985, p. 191. R. Benassi, U. Folli, L. Schenetti and F. Taddei, Adv. Heterocycl. Chem., 41 (1987) 75.
3. For reviews, see: V.N. Sheinker, A.D. Garnovskii and O.A. Osipov, Russian Chem. Rev., 50 (1981) 336 (Uspekhi Khim., 50 (1981) 632). A. Kucsman, and I. Kapovits, in F. Bernadi, I.G. Csizmadia and G. Mangini (Eds.), Organic Sulfur Chemistry: Theoretical and Experimental Advances, Elsevier, Amsterdam, 1985, p. 191. R. Benassi, U. Folli, L. Schenetti and F. Taddei, Adv. Heterocycl. Chem., 41 (1987) 75.
4. For reviews, see: V.N. Sheinker, A.D. Garnovskii and O.A. Osipov, Russian Chem. Rev., 50 (1981) 336 (Uspekhi Khim., 50 (1981) 632). A. Kucsman, and I. Kapovits, in F. Bernadi, I.G. Csizmadia and G. Mangini (Eds.), Organic Sulfur Chemistry: Theoretical and Experimental Advances, Elsevier, Amsterdam, 1985, p. 191. R. Benassi, U. Folli, L. Schenetti and F. Taddei, Adv. Heterocycl. Chem., 41 (1987) 75.
5. Y. Miyahara, T. Inazu and T. Yoshino, J. Org. Chem., 49 (1984) 1177.
6. Y. Miyahara, T. Inazu and T. Yoshino, Tetrahedron Lett., 25 (1984) 415.
7. a. N.L. Allinger, Y.H. Yuh and J.-H. Lii, J. Am. Chem. Soc., 111 (1989) 8551.
8. b. J.-H. Lii and N.L. Allinger, J. Am. Chem. Soc., 111 (1989) 8566.
9. J.-H. Lii and N.L. Allinger, J. Am. Chem. Soc., 111 (1989) 8576.
10. MM3(94) was obtained from QCPE, Indiana University, Bloomington, Indiana, USA.
11. N.L. Allinger, X. Zhou and J. Bergsma, J. Mol. Struct. (Theochem), 312 (1994) 69.
12. MOPAC93, Revision 1, developed by Fujitsu Ltd. Tokyo, Japan, and J.J.P. Stewart, Stewart Computational Chemistry, 1994.
13. J.J.P. Stewart, J. Comput. Chem., 10 (1989) 209 and 221.
14. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc., 107 (1985) 3902.
15. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.V. Gill, M.W. Wong, J.B. Foresman, H.B. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Ragahvachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, J.A. Pople, Gaussian, Inc., Pittsburgh, PA.
16. AMPAC 5.0 is a quantum chemistry program from Simichem, Inc., Shawnee, Kansas, USA. We thank Dr. A.J. Holder for generous permission to use the demonstration version of the program.
17. T. Drakenberg, J.M. Sommer and R. Jost, Org. Magn, Reson., 8 (1976) 579.
18. E.G. Merinova, V.N. Sheinker, M.E. Perel'son and O.A. Osipov, J. Org. Chem. USSR (Zh. Org. Khim), 12 (1976) 597.
19. F.A. Miller, W.G. Fateley and R.E. Witkowski, Spectrochim. Acta, 23A (1967) 891.
20. S.A.M, Vanhommerig, R.J. Meier, L.A.Ae. Sluyterman, and E.M. Meijer, J. Mol, Struct.(Theochem), 304 (1994) 53.
21. S. Nagata, Y. Yamabe, K. Yoshikawa and H. Kato, Tetrahedron, 29 (1973) 2545.
22. a. C. Müller and M.S. Plesset, Phys. Rev., 46 (1934) 618.
23. b. J.A, Pople, J.S. Binkley and T. Seeger, Int. J. Quantum Chem. Symp., 10 (1976) 1.
24. D. Casarini, L. Lunazzi and D. Macciantelli, J. Chem. Soc. Perkin Trans. 2, (1985) 1839.
25. J.J.P. Stewart, J. Comp.-Aided Mol. Design, 4 (1990) 1, p.43. MOPAC 93.00 MANUAL, J.J.P. Stewart and Fujitsu Limited, Tokyo, Japan, 1993, p.203.
26. J.J.P. Stewart, J. Comp.-Aided Mol. Design, 4 (1990) 1, p.43. MOPAC 93.00 MANUAL, J.J.P. Stewart and Fujitsu Limited, Tokyo, Japan, 1993, p.203.
27. B. Coussens, K. Pierloot and R.J. Meier, J. Mol. Struct. (Theochem), 259 (1992) 331.
28. S.A.M. Vanhommerig, R.J. Meier, L.A.Ae. Sluyterman and E.M. Meijer, J. Mol. Struct.(Theochem), 304 (1994) 53.
29. S. Schröder, V. Daggett and P. Kollman, J. Am. Chem. Soc., 113 (1991) 8922.
30. J.A. Bikker and D.F. Weaver, J. Mol. Struct. (Theochem), 281 (1993) 173.
31. K. Kakar, E.E. Rinehart, C.R. Quade and T. Kojima, J. Phys. Chem., 52 (1970) 3805.
32. L. Lunazzi, G. Placucci, C. Chatgihaloglu and D. Macciantelli, J. Chem. Soc. Perkin Trans. 2, (1984) 819.