Artículos de revistas
Substituent-induced Chemical Shifts (scs) Of 1,4-disubstituted Benzenes: Correlation Analysis
Registration in:
Canadian Journal Of Analytical Sciences And Spectroscopy. , v. 45, n. 2, p. 1 - 35, 2000.
12056685
2-s2.0-0034354283
Author
Do Canto E.L.
Tasic L.
Rittner R.
Institutions
Abstract
The 13C NMR Substituent-induced Chemical Shifts (SCS) of aromatic carbons in 1,4-disubstituted benzenes were correlated with inductive and mesomeric effects, expressed in σI and σR (NMR) scales, and with charge alterations (Δ) provoked by introducing a new substituent (X) at position C-1. 105 different compounds with groups attached to C-1 (X) and C-4 (Y) in a sequence: NMe2, NH2, OMe, F, Cl, Br, Me, H, CF3, CN, C(O)OEt, C(O)Me, NO2 and CHO were studied. Correlations of σI and σR with SCS and with Δq, and of SCS with Δq, showed statistical relevance just for C-4. SCS and Δq were correlated only with σR for C-2. No correlation was found for C-1 (ipso-carbon), except between Δq and σR, while for C-3 the occurrence or not of any correlation was strongly dependent on the classes of compounds, fixed by the substituent at C-4 (Y). 45 2 1 35 Bromilow, J., Brownlee, R.T.C., Craik, D.J., Sadek, M., Taft, R.W., (1980) J. Org. Chem., 45, p. 2429 Fadhil, G.F., (1992) Z. Naturforsch., 47 A, p. 775 Bromilow, J., Brownlee, R.T.C., Craik, D.J., Sadek, M., (1986) Magn. Reson. Chem., 24, p. 862 Ludwig, M., Wold, S., Exner, O., (1992) Acta Chem. Scand., 46, p. 549 Brownlee, R.T.C., Sadek, M., (1981) Aust. J. Chem., 34, p. 1593 Ehrenson, S., (1979) J. Org. Chem., 44, p. 1793 Krygowski, T.M., Häfelinger, G., Schüle, J., (1986) Z. Naturforsch., 41 B, p. 895 Bock, C.W., Trachtman, M., George, P., (1985) J. Mol. Struct., 122, p. 155 Sadova, N.I., Vilkov, L.V., (1982) Russ. Chem. Rev. (Engl. Transl.), 51, p. 87 March, J., (1992) Advanced Organic Chemistry, 4th Ed., pp. 19-22. , Wiley, New York Stewart, J., (1990) "Mopac Manual". 6th Ed., , Frank J. Seiler Research Laboratory, U. S. Air Force Academy Burkert, U., Allinger, N.L., (1982) Molecular Mechanics, 1st Ed., , American Chemical Society, Washington, chapter 3 Dodge, M., Kinata, C., Stinson, C., (1995) MS Excel 5 for Windows, 1st Ed., , Microsft Press-Makron Books, São Paulo Box, G.E.P., Hunter, W.G., Hunter, J.S., (1978) Statistics for Experimenters, , Wiley, London Canto, E.L., Rittner, R., (1990) I Jornada Brasileira de Ressonância Magnética, , Rio de Janeiro Bromilow, J., Brownlee, R.T.C., Lopez, V.O., Taft, R.W., (1979) J. Org. Chem., 44, p. 4766 Wells, P.R., Ehrenson, S., Taft, R.W., (1968) Prog. Phys. Org. Chem., 6, p. 147 Mendenhall, W., Sincich, T., (1988) "Statistics for the Engineering and Computer Sciences". 2nd Ed., , Deelen-Macmillan, London, chapter 11 Hehre, W.J., Taft, R.W., Topsom, R.D., (1976) Prag. Phys. Org. Chem., 12, p. 159 Budesínsky, M., Johnels, D., Edlund, U., Exner, O., (1991) Collect. Czech. Chem. Commun., 56, p. 368