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The Kinetic Order of an Interfacial Diels–Alder Reaction Depends on the Environment of the Immobilized Dienophile
Author(s) -
Yousaf Muhammad N.,
Chan Eugene W. L.,
Mrksich Milan
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000602)39:11<1943::aid-anie1943>3.0.co;2-#
Subject(s) - diels–alder reaction , alder , kinetic energy , order (exchange) , chemistry , catalysis , organic chemistry , physics , biology , classical mechanics , ecology , economics , finance
Cyclic voltammetry has been used to study the kinetics of the Diels–Alder reaction of cyclopentadiene with quinone immobilized on a monolayer (see scheme). By monitoring the reduction in current as the redox‐active quinone is converted into the redox‐inactive adduct, the reaction was shown to proceed with a second‐order rate constant when hydroxyl groups were incorporated into the monolayer (X=OH), but with a first‐order rate constant when methyl groups were incorporated (X=CH 3 ).