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Mechanism of electrophilic aromatic substitutions: Comments on a recent criticism concerning the use of the mesitylene/durene reactivity ratio as a probe to distinguish between ionic and et pathways
Author(s) -
Baciocchi Enrico,
Galli Carlo
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080808
Subject(s) - chemistry , mesitylene , durene , electrophile , reactivity (psychology) , ionic bonding , mechanism (biology) , electrophilic aromatic substitution , computational chemistry , organic chemistry , photochemistry , benzene , ion , epistemology , philosophy , medicine , alternative medicine , pathology , catalysis
As a rebuttal to recent criticisms aimed at the mechanistic significance of the determination of the mesitylene/durene relative reactivity, it is argued that this ratio does provide reliable information about the structure of the transition state of many S E Ar reactions, supporting the operation of the ‘conventional’ ionic mechanism, as opposed to the ET mechanism. Not even in the case of competitive experiments does it appear that the criticisms are justified.