Artículos de revistas
Substituent-induced 1h Chemical Shifts Of 3-substituted Camphors
Registration in:
Magnetic Resonance In Chemistry. , v. 35, n. 9, p. 609 - 613, 1997.
7491581
2-s2.0-0031533736
Author
Kaiser C.R.
Rittner R.
Basso E.A.
Institutions
Abstract
The high-field 1H NMR analysis of 3-substituted camphors with OH, OMe, SMe, NHMe, NMe2 and Me substituents at endo and exo positions, and also with an oxo substituent, is reported. The substituent-induced chemical shifts (SCS) obtained for these difunctional systems, including those from previous work on 3-halocamphors, were examined in view of multilinear correlations with steric and electronic parameters. The resultant data show a strong contribution from the electric field mechanism, principally for the protons closer to the substituent. Carbonyl group interference on the expected SCS for the α-proton is also observed, with less deshielding than those of substituted bornanes and norbornanes. © 1997 by John Wiley & Sons, Ltd. 35 9 609 613 Breitmaier, E., Voelter, W., (1987) Carbon-13 NMR Spectroscopy, 3rd Ed., , VCH, Weinheim and references cited therein Zurcher, R.F., (1967) Prog. Nucl. Magn. Reson. Spectrosc., 2, p. 205 Abraham, R.J., Fisher, J., (1985) Magn. Reson. Chem., 23, p. 862. , and references cited therein ApSimon, J.W., Beierbeck, H., (1971) Can. J. Chem., 49, p. 1328 Schneider, H.J., Buchheit, U., Becker, N., Schmidt, G., Siehl, U., (1986) J. Am. Chem. Soc., 107, p. 7027 Schneider, H.J., Buchheit, U., Hoppen, V., Schmidt, G., (1989) Chem. Ber., 122, p. 321 Schneider, H.J., Buchheit, U., Becker, N., Schmidt, G., Siehl, U., (1985) J. Am. Chem. Soc., 107, p. 7027 Abraham, R.J., Barlow, A.P., Rowan, A.E., (1989) Magn. Reson. Chem., 27, p. 1074 Basso, E.A., Kaiser, C.R., Rittner, R., Lambert, J.B., (1994) Magn. Reson. Chem., 32, p. 205 Kaiser, C.R., Rittner, R., Basso, E.A., (1994) Magn. Reson. Chem., 32, p. 503 Charton, M., Motoc, I., (1983) Top. Curr. Chem., 114, p. 57 Charton, M., (1975) J. Am. Chem. Soc., 97, p. 1552 Taft, R.W., Topsom, R.D., (1987) Prog. Phys. Org. Chem., 16, p. 1 Reynolds, W.F., Gomes, A., Maron, A., MacIntyre, D.W., Tanin, A., Hamer, G.K., Peat, I.R., (1983) Can. J. Chem., 61, p. 2376 Marriott, S., Topsom, R.D., (1984) J. Am. Chem. Soc., 106, p. 7 Altona, C., Ippel, J.H., Hoekzema, A.J.A.W., Erkelens, C., Groesbeek, M., Donders, L.A., Chem, M.R., 27, 504, p. 1989 Basso, E.A., Kaiser, C.R., Rittner, R., Lambert, J.B., (1993) J. Org. Chem., 58, p. 7865 Sanders, J.K.M., Mersh, J.D., (1983) Prog. Nucl. Magn. Reson. Spectrosc., 15, p. 353 Aue, W.P., Bartholdi, E., Ernst, R.R., (1976) J. Chem. Phys., 64, p. 2229 Bax, A., (1983) J. Magn. Reson., 53, p. 517 Scholz, D., (1983) Synthesis, p. 944 Hutchinson, J.H., Money, T., (1984) Can. J. Chem., 62, p. 1899 Daniel, A., Pavia, A.A., (1971) Bull. Soc. Chim. Fr., 3, p. 1060 Hassner, A., Reuss, R.H., Pinnick, H.W., (1975) J. Org. Chem., 40, p. 3427