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Kinetic modeling of the crosslinking reaction of cycloaliphatic epoxides with carboxyl functionalized acrylic resins: Hammett treatment of cycloaliphatic epoxides
Author(s) -
Soucek M. D.,
AbuShanab O. L.,
Anderson C. D.,
Wu S.
Publication year - 1998
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19980601)199:6<1035::aid-macp1035>3.0.co;2-p
Subject(s) - chemistry , benzoic acid , hammett equation , polymer chemistry , nucleophile , reactivity (psychology) , organic chemistry , catalysis , kinetics , reaction rate constant , medicine , physics , alternative medicine , pathology , quantum mechanics
Cyclohexene oxide and benzoic/substituted benzoic acids were used as model compounds to study the reactivity of cycloaliphatic diepoxides with carboxyl functionalized polymers. A σ‐ρ Hammett treatment of cycloaliphatic epoxides with substituted benzoic acids was used to investigate the reaction mechanism(s) of ester formation. The catalytic dependence on the acid strength was obtained via a H 0 Hammett‐Deyrup acidity function. The σ‐ρ Hammett treatment resulted in a positive ρ indicating that the transition state or the activated complex has a developing negative charge. This suggests that only the dissociated benzoic acid (or substituted benozic acids) is the attacking nucleophile.