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Methyl Group Rotation Driven by Proton Transfer through a Long‐Range Chemical Interaction
Author(s) -
Ushiyama Hiroshi,
Takatsuka Kazuo
Publication year - 2005
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/anie.200461459
Subject(s) - hyperconjugation , rotation (mathematics) , proton , chemistry , coupling (piping) , tautomer , group (periodic table) , molecule , transfer (computing) , chemical physics , computational chemistry , methyl group , stereochemistry , physics , computer science , quantum mechanics , materials science , organic chemistry , metallurgy , artificial intelligence , parallel computing
Coupling drives the rotation : A theoretical study of proton‐transfer dynamics of 5‐methyltropolone (5MTR) has identified a long‐range mechanical interaction. Methyl group rotation can be driven by proton transfer because of coupling between hyperconjugation and tautomerization within 5MTR (see HOMO–LUMO interaction). A quantum‐mechanical mechanism is presented in which this molecule undergoes a conformational change.