Influence of the C-H⋯N intramolecular interaction on the spatial structures and 1H and 13C NMR parameters of heteroaryl vinyl ethers and sulfides

Magnetic Resonance in Chemistry

Volumn 41, Issue 8, 2003, Pages 557-566

  Afonin, Andrei V ^a   Ushakov, Igor A ^b   Kuznetsova, Svetlana Yu ^b   Andriyankova, Lyudmila V ^a  

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

^b IRKUTSK NATIONAL RESEARCH TECHNICAL UNIVERSITY   (Russian Federation)

Author keywords

13C NMR; 1H NMR; C H N hydrogen bonding; Heteroaryl vinyl ethers; Heteroaryl vinyl sulfides; Intramolecular interactions; NMR

Indexed keywords

ETHERS; HYDROGEN; SULFUR COMPOUNDS;

13C NMR; 1H NMR; C-H⋯N HYDROGEN BONDING; HETEROARYL VINYL ETHER; HETEROARYL VINYL SULPHIDE; HETEROARYLS; INTRAMOLECULAR INTERACTIONS; SPATIAL STRUCTURE; VINYL ETHERS;

HYDROGEN BONDS;

ALKYL GROUP; CARBON; ETHER DERIVATIVE; HYDROGEN; NITROGEN; SULFIDE; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ELECTRON; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY;

EID: 0142024196     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1215     Document Type: Article

References (46)

1. Afonin AV, Voronov VK, Andriyankov MA. Zh. Obshch. Khim. 1986; 56: 2806.
2. Afonin AV, Voronov VK, Trzhtsinskaya BV, Andriyankov MA, Teterina LF, Stepanova ZV. Izv. Akad. Nauk SSSR, Ser. Khim. 1987; 1753.
3. Afonin AV, Ushakov IA, Kuznetsova SYu, Petrova OV, Schmidt EYu, Mikhaleva AI. Magn. Reson. Chem. 2002; 40: 114.
4. Afonin AV, Voronov VK, Andriyankov MA, Danovich DK. Izv. Akad. Nauk SSSR, Ser. Khim. 1987; 317.
5. (a) Afonin AV, Andriyankov MA. Zh. Org. Khim. 1988; 24: 1034;
6. (b) Afonin AV. Izv. Akad. Nauk SSSR, Ser. Khim. 1991; 1344;
7. (c) Afonin AV. Izv. Akad. Nauk SSSR, Ser. Khim. 1991; 2289.
8. Afonin AV, Vashchenko AV, Fujiwara H. Bull. Chem. Soc. Jpn. 1996; 69: 933.
9. Afonin AV, Vashchenko AV, Takagi T, Kimura A, Fujiwara H. Can. J. Chem. 1999; 77: 416.
10. Sugiura M, Vashchenko AV, Kimura A, Fujiwara H. J. Chem. Soc., Perkin Trans.2 2000; 1489.
11. Donahue J. In Selected Topics in Hydrogen Bonding in Structural Chemistry and Molecular Biology, Rich A, Davidson N (eds), Freeman: San Francisco, 1968; 443.
12. (a) Steiner T. Crystallogr. Rev. 1996; 6: 1;
13. (b) Desiraju GR. Acc. Chem. Res. 1996; 29: 441;
14. (c) Desiraju GR, Steiner T. The Weak Hydrogen Bond: Applications to Structural Chemistry and Biology. Oxford University Press: New York, 1999;
15. (d) Bishop R, Marjo CE, Scudder ML. Mol. Cryst. Liq. Cryst., Sect. A 1998; 313: 75.
16. (a) Popelier PLA, Bader RFW. Chem. Phys. Lett. 1992; 189: 542;
17. (b) Law RV, Sasanuma Y. J. Chem. Soc., Faraday Trans. 1996; 92: 4885;
18. (c) Novoa JJ, Lafuente P, Mota F. Chem. Phys. Lett. 1998; 290: 519;
19. (d) Peralta JE, Ruiz de Azua MC, Contreras RH. J. Mol. Struct. (Theochem) 1999; 491: 23;
20. (e) Masunov A, Dannenberg JJ, Contreras RH. J. Phys. Chem. 2001; 105: 4737.
21. Jeffrey GA. J. Mol. Struct. 1999; 485: 293.
22. Amosova SV, Gostevskaya VI, Gavrilova GM, Afonin AV. Zh. Org. Khim. 2003; in press.
23. Scvortsocva GG, Kim DG, Andriyankova LV. Khim. Geterotsikl. Soedin. 1978; 364.
24. Andriyankov MA, Nikitin MV, Afonin AV. Izv. Akad. Nauk SSSR, Ser. Khim. 1989; 2098.
25. (a) Levy GC, Nelson GL. Carbon-13 Nuclear Magnetic Resonance for Organic Chemists. Wiley: New York, 1972;
26. (b) Stothers JB. Carbon-13 Nuclear Magnetic Resonance. Academic Press: New York, 1972;
27. (c) Vogeli U, Philipsborn W. Org. Magn. Reson. 1973; 5: 551;
28. (d) Su J-A, Siew E, Brown EV, Smith SL. Org. Magn. Reson. 1977; 10: 122;
29. (e) Su J-A, Siew E, Brown EV, Smith SL. Org. Magn. Reson. 1978; 11: 575;
30. (f) Joseph-Nathan P, Garcia-Martinez C, Morales-Rios MS. Org. Magn. Reson. 1990; 28: 311.
31. Voronov VK, Keyko VV, Moskovskaya TE. Zh. Strukt. Khim. 1977; 18: 917.
32. Bzhezovskiy VM, Kalabin GA, Aliev IA, Trofimov BA, Shahgel'diev MA, Kuliev AM. Izv. Akad. Nauk SSSR, Ser. Khim. 1976; 1999.
33. Afonin AV, Vashchenko AV, Voronov VK, Trzhtsinskaya BV, Abramova ND, Stepanova ZV, Andriyankov MA. Zh. Org. Khim. 1990; 26: 411.
34. Afonin AV, Vashchenko AV, Contreras RH. Zh. Org. Khim. 1997; 33: 1507.
35. Meot-Ner (Mautner) M. J. Am. Chem. Soc. 1979; 101: 2396.
36. (a) Vizioli C, Ruiz de Azua MC, Giribet CG, Contreras RH, Turi L, Dannenberg JJ, Rae ID, Weingold JA, Malagoli M, Zanasi R, Lazzeretti P. J. Phys. Chem. 1994; 98: 8858;
37. (b) Giribet CG, Vizioli C, Ruiz de Azua MC, Contreras RH, Dannenberg JJ, Masunov A. J. Chem. Soc., Faraday Trans. 1996; 92: 3029;
38. (c) Dannenberg JJ, Haskamp L, Masunov A. J. Phys. Chem. A. 1999; 103: 7083.
39. (a) Biekofsky RR, Pomilio AB, Contreras RH, de Kowalewski DG, Facelli JC. Magn. Reson. Chem. 1989; 27: 158;
40. (b) Contreras RH, Biekofsky RR, de Kowalewski DG, Orendt AM, Facelli JC. J. Phys. Chem. 1993; 97: 91;
41. (c) Biekofsky RR, Pomilio AB, Aristegui RA, Contreras RH. J. Mol. Struct. 1995; 344: 143;
42. (d) de Kowalewsky DG, Kowalewsky VJ, Botek E, Contreras RH, Facelli JC. Magn. Reson. Chem. 1997; 35: 351;
43. (e) Peralta JE, Ruiz de Azua MC, Contreras RH. Int. J. Quantum Chem. 1998; 70: 105.
44. Bax A, Freeman R, Frenkiel TA. J. Am. Chem. Soc. 1981; 103: 2102.
45. (a) Scvortsocva GG, Tirina SM, Voronov VK. Khim. Geterotsikl. Soedin. 1971; 798;
46. (b) Scvortsocva GG, Andriyankov MA, Stepanova ZV, Kashik TV, Ponomareva SV, Kim DG. Khim. Geterotsikl. Soedin. 1976; 375.