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Biomimetic Catalysis of an S N 2 Reaction Resulting from a Novel Form of Transition‐State Stabilization
Author(s) -
Stauffer David A.,
Barrans Richard E.,
Dougherty Dennis A.
Publication year - 1990
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.199009151
Subject(s) - catalysis , quinoline , methylation , methyl iodide , chemistry , iodide , transition (genetics) , combinatorial chemistry , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , biochemistry , gene
A cation – π‐electron interaction is the essential factor responsible for the stabilization of the transition state during the methylation of quinoline (and related bases) with methyl iodide by a cage host compound (see picture on the right). The stabilization results in a catalytic effect: In the presence of the host the reaction is accelerated by a factor of 100. The system provides a primitive model for enzymatic methylation.
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