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Influence of a Side-Chain on Deuterium Isotope Effects in C-13 NMR Spectra of Some Benzene Derivatives (CROSBI ID 79296)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Novak, Predrag ; Vikić-Topić, Dražen ; Meić, Zlatko ; Gacs-Baitz, Eszter Influence of a Side-Chain on Deuterium Isotope Effects in C-13 NMR Spectra of Some Benzene Derivatives // Magnetic resonance in chemistry, 34 (1996), 8; 610-615. doi: 10.1002/(SICI)1097-458X(199608)34:8<610::AID-OMR938>3.0.CO;2-O

Podaci o odgovornosti

Novak, Predrag ; Vikić-Topić, Dražen ; Meić, Zlatko ; Gacs-Baitz, Eszter

engleski

Influence of a Side-Chain on Deuterium Isotope Effects in C-13 NMR Spectra of Some Benzene Derivatives

Deuterium-induced isotope effects on C-13 chemical shifts were measured in a series of benzene derivatives, viz, toluene, benzoic acid and benzophenone, The effects over two, three and four bonds reflect a dependence on the transmission pathway and the nature of the side-chain. Steric and inductive influences of side-chain lane pair electrons located at the P-position to the phenyl ring account for a lower magnitude and negative sign of some effects in the deuteriated phenyl ring. In monodeuteriated benzophenones isotope effects are transmitted to the second phenyl ring, e.g. in p-deuteriobenzophenone over up to nine bonds, Although the carbonyl group allows only a minor conjugation between the phenyl rings, the extent, the magnitude and the sign of isotope effects resemble those in fully conjugated molecules, indicating a similar transmission mechanism. In polydeuteriated isotopomers, the additivity of isotope effects holds for the majority of carbon atoms. However, in few cases significant deviations exist owing to perturbations in hydrogen-bond dynamics and redistribution of rotamer populations caused by deuteriation, For monodeuteriated isotopomers, a number of C-13-H-2 coupling constants through one and three bonds are also reported.

C-13 NMR ; Deuterium isotope effects ; Toluene ; Benzoic acid ; Benzophenone

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Podaci o izdanju

34 (8)

1996.

610-615

objavljeno

0749-1581

1097-458X

10.1002/(SICI)1097-458X(199608)34:8<610::AID-OMR938>3.0.CO;2-O

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