ELECTRONIC AND GEOMETRIC STRUCTURE OF FLUORINE-SUBSTITUTED BENZYL RADICALS

ELECTRONIC AND GEOMETRIC STRUCTURE OF FLUORINE-SUBSTITUTED BENZYL RADICALS Full article

Journal

Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
ISSN: 0568-5230

Output data

Year: 1990, Volume: 39, Number: 5, Pages: 956-961 Pages count : 6 DOI: 10.1007/BF00961690

Authors

Beregovaya I.V. ¹ , Shchegoleva L.N. ¹ , Platonov V.E. ¹

Affiliations

1	Novosibirsk Institute of Organic Chemistry Siberian Branch, Academy of Sciences of the USSR, USSR

According to the data from quantum-chemical calculations and theoretical analysis, the effect of fluorine atoms on the electronic and stereochemical structure of the benzyl radical depends substantially on their position. Fluorine atoms in the ring hinder the out-of-plane distortions of the CH2 group, and substituted C6F(n)H(5-n)-CH2 radicals are accordingly planar-pi-radicals. On the other hand, the presence of alpha-fluorine atoms assists pyramidal deformation of the methylene fragment, leading in the case of the alpha, alpha-difluoro-substituted compounds to the formation of nonplanar pseudo-pi-radical structures. Here the fluorine atoms in the ring at the p and o positions should increase somewhat while those at the m positions should reduce the capacity of the CF2 group for deformation.

Beregovaya I.V. , Shchegoleva L.N. , Platonov V.E.
ELECTRONIC AND GEOMETRIC STRUCTURE OF FLUORINE-SUBSTITUTED BENZYL RADICALS
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 1990. V.39. N5. P.956-961. DOI: 10.1007/BF00961690 WOS Scopus РИНЦ

Published print:

May 1, 1990

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