Title

Molecular Structures of the Metastable Charge-Transfer Complexes of Benzene (and Toluene) With Bromine as the Pre-Reactive Intermediates in Electrophilic Aromatic Bromination

Document Type

Article

Language

eng

Publication Date

1-2002

Publisher

Royal Society of Chemistry

Source Publication

New Journal of Chemistry

Source ISSN

1144-0546

Abstract

Successful crystallization and X-ray crystallographic analyses of the highly metastable (1∶1) complexes of bromine with benzene and toluene establish the unique (localized) structure B that differs in notable ways from the long-accepted (delocalized) structure A. Furthermore, we demonstrate the (highly structured) charge-transfer complexes [C6H6,Br2] and [CH3C6H5,Br2] to be the pre-reactive intermediates that are converted (via an overall Br+ transfer) to the Wheland intermediates in electrophilic aromatic bromination. The role of the dative ion pairs [C6H6˙+ Br2˙] and [CH3C6H5˙+ Br2˙] in the rate-limiting activation processes is underscored.

Comments

New Journal of Chemistry, Vol. 26, No. 5 (2002): 582-592. DOI.

Sergey V. Lindeman was affiliated with the University of Houston at the time of publication.

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