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Stereodynamics of bond rotation in tertiary 1‐naphthoic acid amides: A computational study
Author(s) -
Campomanes Pablo,
Menéndez M. Isabel,
López Ramón,
Sordo Tomás L.
Publication year - 2005
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.20172
Subject(s) - coalescence (physics) , equivalence (formal languages) , rotation (mathematics) , chemistry , gibbs free energy , computation , computational chemistry , thermodynamics , mathematics , physics , pure mathematics , geometry , algorithm , astrobiology
Computations sho that independent NCO rotation is not possible in N,N‐ diethyl‐1‐naphthamide, and that the coalescence signal corresponding to methyl equivalence observed in the VT NMR spectrum of this system is caused by a complex process whose rate‐determining step implies concerted NCO, ArCO, and ethyl rotations. The calculated Gibbs energy barriers for these processes in solution are in good agreement with the experimental values. © 2005 Wiley Periodicals, Inc. J Comput Chem 26: 365–373, 2005