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Reaction of para ‐Hydroxy‐Substituted Diphenylmethanes with tert ‐Butoxy Radical
Author(s) -
Correia Catarina F.,
Borges dos Santos Rui M.,
Estácio Sílvia G.,
Telo João P.,
Costa Cabral Benedito J.,
Martinho Simões José A.
Publication year - 2004
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.200400044
Subject(s) - chemistry , acetonitrile , electron paramagnetic resonance , molecule , hydrogen atom , photochemistry , medicinal chemistry , hydrogen bond , group (periodic table) , organic chemistry , nuclear magnetic resonance , physics
What is the outcome of this reaction? In acetonitrile solution, the methylenic CH bond is approximately 25 kJ mol −1 weaker than the OH bond in the same molecule (see picture), as demonstrated by time‐resolved photoacoustic calorimetry and quantum chemical methods. However, as shown by electron spin resonance spectroscopy, the tert ‐butoxy radical selectively abstracts the hydrogen atom from the OH group.