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Electrophilicities of Bissulfonyl Ethylenes
Author(s) -
Asahara Haruyasu,
Mayr Herbert
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201101046
Subject(s) - carbanion , nucleophile , electrophile , reactivity (psychology) , chemistry , reaction rate constant , computational chemistry , kinetics , sulfur , ylide , medicinal chemistry , organic chemistry , physics , catalysis , quantum mechanics , medicine , alternative medicine , pathology
Kinetics of the reactions of bissulfonyl ethylenes with various carbanions, a sulfur ylide, and siloxyalkenes have been investigated photometrically at 20 °C. The second‐order rate constants have been combined with the known nucleophile‐ specific parameters N and s N for the nucleophiles to calculate the empirical electrophilicity parameters E of bissulfonyl ethylenes according to the linear free energy relationship log k (20 °C)= s N ( N + E ). Structure‐reactivity relationships are discussed, and it is shown that the electrophilicity parameters E derived in this work can be employed to define the synthetic potential of bissulfonyl ethylenes as Michael acceptors.