F. J. Koer, C. Altona
Sep 2, 2010
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Recueil des Travaux Chimiques des Pays-Bas
Abstract
Fourier transform carbon-13 NMR spectra of a series of 3-(X-phenyl)glutaric anhydrides [X: H (2),4-F (3), 4-Cl (4), 4-Br (5), 4-OCH3 (6), 4-NO2 (7), 3-Cl (8) and 2,6-Cl2 (9)] and of 3-methyl-3-(4-chlorophenyl)- (10)-, 3,3-diphenyl- (11)- and 3,3-(2,2′-biphenylylene)-glutaric anhydride (12) have been obtained and interpreted. Spectral assignments of the aromatic side-chain carbons for 3–9 were made with the aid of additive parameters derived from suitably substituted toluenes for which unequivocal assignments are possible. The carbon-13 and proton chemical shift data of the glutaric anhydride skeletal carbons and appended protons are compared and discussed in terms of conformational properties of the anhydride ring and its side-chain. A set of substituent parameters (α: 17.6 ± 0.3 ppm, β: +7.0 ± 0.3 ppm and γ: −1.3 ± 0.3 ppm), which correlates the average effect of the XC6H4 nucleus on the chemical shifts of the glutaric anhydride ring carbon atoms in 2–8, has been generated.