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Substituent effects on the CC bond strength, 17 . Formation and stability of α‐carbamoylbenzyl radicals
Author(s) -
Züffle Stephan,
Beckhaus HansDieter,
Rüchardt Christoph
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199505127
Subject(s) - homolysis , chemistry , radical , steric effects , substituent , standard enthalpy of formation , bond strength , medicinal chemistry , kinetics , photochemistry , stereochemistry , organic chemistry , physics , adhesive , layer (electronics) , quantum mechanics
Products and kinetics of the homolytic thermolyses reactions of the three tertiary amides 6a–c of 2,3,3‐triphenylpropanoic acid were studied in solution. The steric effects on the C‐C bond homolysis processes were evaluated from MM2 calculations. Taking this into account, we deduced radical stabilization enthalpies RSE for the α‐carbamoylbenzyl radicals 3a–c from the activation enthalpies ΔH ≠ [ RSE (kcal/mol): 8.3 ± 2.8 ( 3a ), 10.3 ± 2.7 ( 3b ), 9.0 ± 2.2 ( 3c )].