Artículos de revistas
Intramolecular Interactions In α-mono-substituted Acetic Acids Through 13c Nmr Chemical Shifts And Theoretical Calculations
Registro en:
Canadian Journal Of Analytical Sciences And Spectroscopy. , v. 45, n. 05/06/15, p. 148 - 153, 2000.
12056685
2-s2.0-0034561234
Autor
Freitas M.P.
Campos M.G.
Tormena C.F.
Rittner R.
Institución
Resumen
13C NMR chemical shifts for some α-heterosubstituted acetic acids are reported. The α-methylene carbon presents high ICS ("Intramolecular Interaction Chemical Shifts") values, which are very similar to those of other series of carbonyl compounds. Neither the ICS or the SCS ("Substituent induced Chemical Shifts") correlate with the usual substituent electronic and/or steric parameters. Those experimental chemical shifts are very close to the ones obtained by theoretical calculations (MP2). The carbonyl carbon chemical shifts also deviate from the empirically calculated values, but are similar to the theoretically estimated shifts (DFT). These observations indicate that, while the theoretically calculated values match the experimental values, the same does not occur with the ones obtained by empirical methods, which can be valuable tools for checking the occurrence of significant intramolecular interactions between two substituents attached to the same methylene carbon atom. 45 05/06/15 148 153 Grant, D.M., Paul, E.G., (1964) J. Am. Chem. Soc., 86, p. 2984 Stothers, J.B., (1972) Carbon-13 NMR Spectroscopy, , Academic Press, New York Martin, G.J., Martin, M.L., Odiot, S., (1975) Org. Magn. Reson., 7, p. 2 Rittner, R., (1985) Quim. Nova, 8, p. 170 Breitmaier, E., Voelter, W., (1987) Carbon-13 NMR Spectroscopy, , 3rd ed., VCH, Weinheim Duddeck, H., (1986) Top. Stereochem., 16, p. 219 Rittner, R., (1987) Recent Advances in Organic NMR Spectroscopy, , J. B. Lambert and R. Rittner (eds.), Norell Press, Landisville Rittner, R., Vanin, J.A., Wladislaw, B., (1988) Magn. Reson. Chem., 26, p. 51 Rittner, R., Martins, M.A.P., Clar, G., (1988) Magn. Reson. Chem., 26, p. 73 Rittner, R., Silva, E.L., Canto, E.L., (1990) Spectrosc. Int. J., 8, p. 173 Rittner, R., Canto, E.L., Grehs, J., (1991) Spectros Copy, 9, p. 31 Rittner, R., Braibante, M.E.F., (1992) Magn. Reson. Chem., 30, p. 420 Basso, E.A., Kaiser, C.R., Rittner, R., Lambert, J.B., (1994) Magn. Reson. Chem., 32, p. 205 Eloranta, J., Hu, J., Suontamo, R., Kolehmainen, E., Knuutinen, J., (2000) Magn. Reson. Chem., 38, p. 205 Foresman, J.B., Frish, A., (1996) Exploring Chemistry with Electronic Structure Methods, 2nd Ed., , Gaussian, Pittsburgh, PA Frisch, M.J., Trucks, C.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998), Gaussian Inc., Pittsburgh, PAInamoto, N., Masuda, S., (1982) Chem. Lett., p. 1007 Hansch, C., Leo, A., Hoeckman, D., (1995) Exploring QSAR - Hydrophobic, Electronic, and Steric Constants, , A.C.S., Washington DC Charton, M., (1987) Prog. Phys. Org. Chem., 16, p. 287 Charton, M., (1983) Top. Curr. Chem., 114, p. 57 Spiesecke, H., Schneider, W.G., (1961) J.Chem.Phys., 35, p. 722 Sofia, R.C.R., (1996), M.Sc. Thesis, Universidade Estadual de CampinasTanaka, S., Toda, S., Nagoya, C., Kanotha, K., Hashimoto, S., Musha, K., Yamaguchi, K., (1975) Bunseki Kagaku, 24, p. 553 Stothers, J.B., Lauterbur, P.C., (1964) Can. J. Chem., 42, p. 1563 Eisenstein, O., Ahn, N.T., Devaquet, J.A., Cantacuzène, J., Salem, L., (1974) Tetrahedron, 30, p. 1717 Metzger, P., Casadevall, E., Casadevall, A., Pouet, M.J., (1980) Can. J. Chem., 58, p. 1503 Olivato, P.R., Rittner, R., (1996) Rev. Heteroatom Chem., 15, p. 115