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The Effect of Solvent on the Stability of mero‐Substituted Alkyl Radicals
Author(s) -
Beckhaus HansDieter,
Rüchardt Christoph
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198707701
Subject(s) - chemistry , enthalpy , alkyl , solvent , radical , mesitylene , polar , succinic anhydride , dissociation (chemistry) , ether , organic chemistry , polymer chemistry , medicinal chemistry , photochemistry , thermodynamics , benzene , physics , astronomy
The “captodative effect”—does it indeed exist? Neither the reaction enthalpy nor the activation enthalpy for the dissociation of 2 (R C 6 H 5 ; t ‐C 4 H 9 ) decreases in polar solvents (ethylene glycol, succinic anhydride, N ‐methylacetamide) in comparison to the values measured in diphenyl ether or mesitylene. This finding contradicts the recently suggested strong stabilization of mero‐ or captodative‐substituted alkyl radicals, such as 1 , by polar solvents.