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The Inherent Competition between Addition and Substitution Reactions of Br 2 with Benzene and Arenes
Author(s) -
Kong Jing,
Galabov Boris,
Koleva Gergana,
Zou JiJun,
Schaefer Henry F.,
Schleyer Paul von Ragué
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101852
Subject(s) - benzene , substitution (logic) , anthracene , naphthalene , phenanthrene , chemistry , substitution reaction , catalysis , electrophilic aromatic substitution , medicinal chemistry , computational chemistry , combinatorial chemistry , organic chemistry , computer science , programming language
Tug of war : Comprehensive DFT computational exploration of the reaction mechanisms predicts that the barriers for Br 2 addition processes to benzene, naphthalene, anthracene, and phenanthrene in isolation (i.e., in the absence of catalysts, see picture) and in simulated CCl 4 solution can be even lower than the barriers for direct substitution. Moreover, substitution products also can arise from stepwise Br 2 addition–HBr elimination routes.