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Quantification of the Nucleophilic Reactivities of Ethyl Arylacetate Anions
Author(s) -
CorralBautista Francisco,
Mayr Herbert
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300265
Subject(s) - chemistry , nucleophile , carbanion , medicinal chemistry , derivative (finance) , reaction rate constant , kinetics , nitro , quinone , nucleophilic addition , computational chemistry , stereochemistry , organic chemistry , catalysis , physics , alkyl , quantum mechanics , financial economics , economics
The kinetics of the reactions of substituted ethyl arylacetates with quinone methides and structurally related diethyl benzylidenemalonates have been studied in DMSO. The second‐order rate constants (lg k 2 ) correlated linearly with the electrophilicities E according to the linear free‐energy relationship lg k 2 = s N ( N + E ), allowing us to determine the nucleophilicity parameters N and s N for these anions. The nucleophilic reactivities of the carbanions vary from N = 27.5 for the parent compound to N = 20.0 for the 4‐nitro‐substituted derivative.