13C-13C Coupling Constants in Structural Studies: XXXII. Additivity of Spin-Spin Couplings in Sterically Strained Heterocycles

Russian Journal of Organic Chemistry

Volumn 39, Issue 5, 2003, Pages 698-704

  Krivdin, L B ^a   Kuznetsova, T A ^a  

^a ANGARSK STATE TECHNICAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

ADDITION REACTION; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COVALENT BOND; MOLECULAR STABILITY; SURFACE PROPERTY; THEORY;

EID: 1642573308     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1026017531015     Document Type: Article

References (45)

1. Krivdin, L.B. and Kalabin, G.A., Prog. NMR Spectrosc., 1989, vol. 21, p. 293.
2. 1H Spin-Spin Couplings in NMR Spectra of Organic Compounds), Novosibirsk: Novosibirsk. Inst. Org. Khim., 1989; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, p. 301; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173.
3. 1H Spin-Spin Couplings in NMR Spectra of Organic Compounds), Novosibirsk: Novosibirsk. Inst. Org. Khim., 1989; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, p. 301; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173.
4. 1H Spin-Spin Couplings in NMR Spectra of Organic Compounds), Novosibirsk: Novosibirsk. Inst. Org. Khim., 1989; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, p. 301; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173.
5. Krivdin, L.B., Trofimov, A.B., Zinchenko, S.V., Glukhikh, N.G., Pestunovich, S.V., Domnin, I.N., Akhachinskaya, T.V., and Donskaya, N.A., Zh. Org. Khim., 1991, vol. 27, p. 1369.
6. Efimov, V.N., Perelyaev, Yu.N., and Krivdin, L.B., Zh. Org. Khim., 1993, vol. 29, p. 1776.
7. Chirkina, E.A., Sergeeva, O.R., and Krivdin, L.B., Russ. J. Org. Chem., 1996, vol. 32, p. 955.
8. Chirkina, E.A., Sergeeva, O.R., and Krivdin, L.B., Russ. J. Org. Chem., 1997, vol. 33, p. 1068.
9. Chirkina, E.A., Sergeeva, O.R., and Krivdin, L.B., Russ. J. Org. Chem., 1999, vol. 35, p. 500.
10. Chirkina, E.A., Sergeeva, O.R., and Krivdin, L.B., Russ. J. Org. Chem., 2000, vol. 36, p. 509.
11. Krivdin, L.B., Kas'yan, L.I., Zinchenko, S.V., Seferova, M.F., and Porubleva, L.V., Zh. Org. Khim., 1990, vol. 26, p. 2482.
12. Kuznetsova, T.A., Istomina, N.V., and Krivdin, L.B., Russ. J. Org. Chem., 1997, vol. 33, p. 1620; ibid., 2000, vol. 36, p. 638.
13. Kuznetsova, T.A., Istomina, N.V., and Krivdin, L.B., Russ. J. Org. Chem., 1997, vol. 33, p. 1620; ibid., 2000, vol. 36, p. 638.
14. Pople, J.A., McIver, J.W., and Ostlund, N.S., J. Chem. Phys., 1968, vol. 49, p. 2960; ibid., 1968, vol. 49, p. 2965; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; ibid., 1973, vol. 58, p. 4714.
15. Pople, J.A., McIver, J.W., and Ostlund, N.S., J. Chem. Phys., 1968, vol. 49, p. 2960; ibid., 1968, vol. 49, p. 2965; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; ibid., 1973, vol. 58, p. 4714.
16. Pople, J.A., McIver, J.W., and Ostlund, N.S., J. Chem. Phys., 1968, vol. 49, p. 2960; ibid., 1968, vol. 49, p. 2965; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; ibid., 1973, vol. 58, p. 4714.
17. Pople, J.A., McIver, J.W., and Ostlund, N.S., J. Chem. Phys., 1968, vol. 49, p. 2960; ibid., 1968, vol. 49, p. 2965; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; ibid., 1973, vol. 58, p. 4714.
18. Pople, J.A. and Beveridge, D.L., Approximate Self-Consistent Molecular Orbital Theory. V. Intermediate Neglect of Differential Overlap, New York: McGraw-Hill, 1970; Pople, J.A., Santry, D.P., and Segal, G.A., J. Chem. Phys., 1965, vol. 43, p. 5129; Pople, J.A., Beveridge, D.L., and Dobosh, P.A., J. Chem. Phys., 1967, vol. 47, p. 2026.
19. Pople, J.A. and Beveridge, D.L., Approximate Self-Consistent Molecular Orbital Theory. V. Intermediate Neglect of Differential Overlap, New York: McGraw-Hill, 1970; Pople, J.A., Santry, D.P., and Segal, G.A., J. Chem. Phys., 1965, vol. 43, p. 5129; Pople, J.A., Beveridge, D.L., and Dobosh, P.A., J. Chem. Phys., 1967, vol. 47, p. 2026.
20. Pople, J.A. and Beveridge, D.L., Approximate Self-Consistent Molecular Orbital Theory. V. Intermediate Neglect of Differential Overlap, New York: McGraw-Hill, 1970; Pople, J.A., Santry, D.P., and Segal, G.A., J. Chem. Phys., 1965, vol. 43, p. 5129; Pople, J.A., Beveridge, D.L., and Dobosh, P.A., J. Chem. Phys., 1967, vol. 47, p. 2026.
21. Diz, A.C., Ruiz de Azua, M.C., Giribet, C.G., and Contreras, R.H., Int. J. Quantum Chem., 1990, vol. 37, p. 663; Contreras, R.H., Giribet, C.G., Ruiz de Azua, M.C., Cavasotto, C.N., Aucar, G.A., and Krivdin, L.B., J. Mol. Struct. (Theochem), 1990, vol. 210, p. 175.
22. Diz, A.C., Ruiz de Azua, M.C., Giribet, C.G., and Contreras, R.H., Int. J. Quantum Chem., 1990, vol. 37, p. 663; Contreras, R.H., Giribet, C.G., Ruiz de Azua, M.C., Cavasotto, C.N., Aucar, G.A., and Krivdin, L.B., J. Mol. Struct. (Theochem), 1990, vol. 210, p. 175.
23. Engelmann, A.R., Natiello, M.A., Scuseria, G.E., and Contreras, R.H., Comput. Phys. Commun., 1986, vol. 39, p. 409; Engelmann, A.R. and Contreras, R.H., Int. J. Quantum Chem., 1983, vol. 23, p. 1033.
24. Engelmann, A.R., Natiello, M.A., Scuseria, G.E., and Contreras, R.H., Comput. Phys. Commun., 1986, vol. 39, p. 409; Engelmann, A.R. and Contreras, R.H., Int. J. Quantum Chem., 1983, vol. 23, p. 1033.
25. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
26. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
27. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
28. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
29. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
30. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
31. Klessinger, M., Megen, H., and Wilhelm, K., Chem. Ber., 1982, vol. 115, p. 50; Stocker, M., Org. Magn. Reson., 1982, vol. 20, p. 175; Klessinger, M. and Cho, J.-H., Org. Magn. Reson., 1983, vol. 21, p. 465; Contreras, R.H. and Scuseria, G.E., Org. Magn. Reson., 1984, vol. 22, p. 411; Cho, J.-H., Klessinger, M., Tecklenborg, U., and Wilhelm, K., Magn. Reson. Chem., 1985, vol. 23, p. 95; Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz de Azua, M.C., and Contreras, R.H., J. Mol. Struct. (Theochem), 1990, vol. 205, p. 63; Della, E.W., Pigou, P.E., Taylor, D.K., Krivdin, L.B., and Contreras, R.H., Aust. J. Chem., 1993, vol. 46, p. 63.
32. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
33. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
34. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
35. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
36. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
37. Frei, K. and Bernstein, H.J., J. Chem. Phys., 1963, vol. 38, p. 1216; Guenther, H. and Herrig, W., Chem. Ber., 1973, vol. 106, p. 3938; Weigert, F.J. and Roberts, J.D., J. Am. Chem. Soc., 1972, vol. 94, p. 6021; Newton, M.D., Schulman, J.M., and Manus, M.M., J. Am. Chem. Soc., 1974, vol. 96, p. 17; Maciel, G.E., McIver, J.W., Ostlund, N.S., and Pople, J.A., J. Am. Chem. Soc., 1970, vol. 92, p. 11; Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1971, vol. 5, p. 211.
38. Oddershede, J. and Jorgensen, P., J. Chem. Phys., 1977, vol. 66, p. 1541.
39. Ramsey, N.F., Phys. Rev., 1953, vol. 91, p. 303.
40. Lukevits, E.Yu., Pudova, O.A., and Sturkovich, R.Ya., Molekulyarnaya struktura kremniiorganicheskikh soedinenii (Molecular Structure of Organosilicon Compounds), Riga: Zinatne, 1988, p. 25.
41. Bartuska, V.J. and Maciel, G.E., J. Magn. Reson., 1972, vol. 7, p. 36.
42. Shcherbakov, V.V., Krivdin, L.B., Glukhikh, N.G., and Kalabin, G.A., Zh. Org. Khim., 1987, vol. 23, p. 1792.
43. Coolidge, M.B. and Stewart, J.J.P., QCPE. Program 455 (Release 6.0), 1990.
44. Schmidt, M.W., Baldridge, K.K., Boatz, J.A, Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S.J., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347.
45. Helgaker, T., Jensen, H.J.A., Joergensen, P., Olsen, J., Ruud, K., Aagren, H., Bak, K.L., Bakken, V., Christiansen, O., Dahle, P., Dalskov, E.K., Enevoldsen, T., Fernandez, B., Heiberg, H., Hettema, H., Jonsson, D., Kirpekar, S., Kobayashi, R., Koch, H., Mikkelsen, K.V., Norman, P., Packer, M.J., Ruden, T.A., Saue, T., Sauer, S.P.A., Sylvester-Hvid, K.O., Taylor, P.R., and Vahtras, O., Dalton: An Electronic Structure Program (Release 1.1), 2000.