Specific intramolecular interactions C-H...N in heteroaryl vinyl ethers and heteroaryl vinyl sulfides studied by 1H, 13C, and 15N NMR spectroscopies and by ab initio calculations on molecular structures as well as on nuclear shieldings

Canadian Journal of Chemistry

Volumn 77, Issue 4, 1999, Pages 416-424

  Afonin, Andrei V ^a   Vashchenko, Alexander V ^b   Takagi, Tatsuya ^b   Kimura, Atsuomi ^c   Fujiwara, Hideaki ^c  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b OSAKA UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY MEDICAL SCHOOL   (Japan)

Author keywords

Ab initio calculation; GIAO; Intramolecular hydrogen bonding; NMR

Indexed keywords

2 VINYLOXYPYRIDINE; 2 VINYLTHIOPYRIDINE; CARBON 13; ETHER DERIVATIVE; HYDROGEN; NITROGEN 15; OXYGEN; PROTON; PYRIDINE DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; MATHEMATICAL COMPUTING; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032867270     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-038     Document Type: Article

References (43)

1. 1. (a) G.C. Pimentel and A.L. McClean. The hydrogen bond. W.H. Freeman, San Francisco. 1960;
2. (b) R.D. Green. Hydrogen bonding by C-H groups. Macmillan, London. 1974;
3. (c) S. Pinchas. J. Phys. Chem. 67, 1862 (1963);
4. (d) M.P. Sammes and R.L. Harlow, J. Chem. Soc. Perkin Trans. 2, 1130 (1976);
5. (e) C. Li and M.P. Sammes. J. Chem. Soc. Perkin Trans. 1, 1303 (1983);
6. (f) J. Chem. Soc. Perkin Trans. 1, 2193 (1983);
7. (g) F.M. Slasinski, J.M. Tustin, F.J. Sweeney, A.M. Armstrong, Q.A. Ahmed, and J.P. Loran. J. Org. Chem. 41, 2693 (1976);
8. (h) R. Houssin and J.-P. Henichart. Org. Magn. Reson. 16, 202 (1981);
9. (i) H. Satonaka, K. Abe, and M. Hirota. Bull. Chem. Soc. Jpn. 61, 2031 (1988).
10. 2. (a) R. Taylor and O. Kennard. J. Am. Chem. Soc. 104, 5063 (1982);
11. (b) D.J. Sutor. J. Chem. Soc. 1105 (1963);
12. (c) R.L. Harlow, S.H. Simonen, C.E. Pfluger, and M.P. Sammes. Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. B30, 2264 (1974);
13. (d) R.L. Harlow, S.H. Simonen, and M.P. Sammes. Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. B32, 2690 (1974);
14. (e) A.N. Chehlov, A. Ju. Aksinenko, A.N. Pushin, and V.B. Sokolov. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 44, 1593 (1995);
15. (f) T. Steiner. J. Chem. Soc. Perkin Trans. 2, 7, 1315 (1995);
16. (g) G.R. Desiraju. Acc. Chem. Res. 24, 290 (1991);
17. (h) Acc.Chem.Res. 29, 441 (1996).
18. 3. A.V. Afonin, A.V. Vashchenko, and H. Fujiwara. Bull. Chem. Soc. Jpn. 69, 933 (1996).
19. 4. F.P.S.C. Gil and J.J.C. Texeira-Dias. Theochem, 363, 311 (1996).
20. 5. R.V. Law and Y. Sasanuma. J. Chem. Soc. Faraday Trans. 92, 4885 (1996).
21. 6. R. Ditchfield. Mol. Phys. 27, 789 (1974).
22. 7. D.B. Chesnut and C.K. Foley. Chem. Phys. Lett. 118, 316 (1985); D.B. Chesnut and K.D. Moore. J. Comput. Chem. 10,648 (1989).
23. 7. D.B. Chesnut and C.K. Foley. Chem. Phys. Lett. 118, 316(1985); D.B. Chesnut and K.D. Moore. J. Comput. Chem. 10, 648 (1989).
24. 8. K. Friedrich, G. Seifert, and G. Grossmann. Z. Phys. D: At. Mol. Clusters, 17, 45 (1990).
25. 9. K. Wolinski, J.F. Hinton, and P. Pulay. J. Am. Chem. Soc. 112, 8251 (1990).
26. 10. G. Schreckenbach and T. Ziegler. J. Chem. Phys. 99, 606 (1995).
27. 11. L.B. Krivdin and G.A. Kalabin. Zh. Org. Khim. 24, 2268 (1988).
28. 12. A. Yu. Denisov, V.J. Mamatyuk, and O.P. Shkurko. Khim. Geterocycl. Soed. 1383 (1985).
29. 13. L.B. Krivdin, V.V. Scherbakov, I.A. Aliev, and G.A. Kalabin. Zh. Org. Khim. 23, 569 (1987).
30. 14. (a) G.A. Kalabin, L.B. Krivdin, V.V. Scherbakov, and B.A. Trofimov. J. Mol. Struct. 143, 569 (1986);
31. (b) L.B.Krivdin and G.A. Kalabin. Prog. Nucl. Magn. Reson. Spectrosc. 21, 293 (1989).
32. 15. S. Li and D.B. Chesnut. Magn. Reson. Chem. 23, 625 (1985).
33. 16. S. Li and D.B. Chesnut. Magn. Reson. Chem. 24, 93 (1986).
34. 17. W.J. Orville-Thomas. Internal rotation in molecules. John Wiley & Sons, London-New York-Sydney-Toronto. 1974.
35. 18. (a) J.E. Del Bene, W.B. Person, and K. Szczepaniak. J. Phys. Chem. 99, 10705 (1995);
36. (b) S. Reiling, J. Brickman, M. Schlenkrich, and P.A. Bopp. J. Comput. Chem. 17, 133 (1996);
37. (c) A. Kovacs, J. Kolossvary, G.J. Csonka, and I. Hargittai. J. Comput. Chem. 17, 1804 (1996).
38. 19. C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
39. 20. O. Kajimoto, M. Kobayashi, and T. Fueno. Bull. Chem. Soc. Jpn. 46, 1422 (1973).
40. 21. P.E. Hansen. Prog. Nucl. Magn. Reson. Spectrosc. 14, 1 (1981).
41. 22. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, and J.A. Pople. Gaussian 94, Revision B.3. Gaussian, Inc., Pittsburgh, Pa. 1995.
42. 23. G.A. Kalabin, D.F. Kushnarev, R.B. Valeyev, B.A. Trofimov, and M.A. Fedotov. Org. Magn. Reson. 18, 1 (1982).
43. 24. V. Wray, L. Ernst, T. Lund, and H.J. Jakobsen. J. Magn. Reson. 40, 55 (1980).