Electrochemical study of some bromo-substituted [2.2]paracyclophanes |
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Authors: | K P Butin A A Moiseeva T V Magdesieva E V Sergeeva V I Rozenberg V G Kharitonov |
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Institution: | (1) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul, Vavilova, 117813 Moscow, Russian Federation |
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Abstract: | The potentials of electrochemical oxidation (
) and reduction (
) of monobromo- and isomeric di- and tribromo2.2]paracyclophanes as well as
of mono-, di-, and tribromobenzenes were measured in acetonitrile. The similarity between the properties ofpseudo-para-disubstituted cyclophanes andmeta-disubstituted benzenes, on the one hand, andpseudo-meta-disubstituted cyclophanes andpara-disubstituted benzenes, on the other hand, was confirmed by the existence of a linear relationship between
of bromo-substituted 2.2]paracyclophanes and
of the corresponding bromo-substituted benzenes. The results were explained in terms of the qualitative theory of molecular orbitals, taking into account a through space interaction between the -systems of the benzene rings.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 839–845, May, 1994.The authors wish to express their gratitude to Professor R. Hoffmann (Cornell University, USA) for a useful discussion and criticisms of the text of this paper.This work was financially supported by the Russian Foundation for Basic Research (Project 93-03-5246). |
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Keywords: | electrochemistry oxidation reduction molecular orbitals [2 2]paracyclophane bromo-subsituted [2 2]paracyclophanes polybromobenzenes |
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