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Residual Enantiomerism and Chromatographic Resolution of a 1,1,2‐Triarylalkene
Author(s) -
Biali Silvio E.,
Rappoport Zvi,
Mannschreck Albrecht,
Pustet Nikola
Publication year - 1989
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.198901991
Subject(s) - enthalpy , isomerization , chemistry , ring (chemistry) , molecule , enantiomer , resolution (logic) , computational chemistry , analytical chemistry (journal) , chromatography , stereochemistry , organic chemistry , thermodynamics , physics , catalysis , artificial intelligence , computer science
A three‐ring flip A⇄B is the isomerization mechanism of lowest activation enthalpy for triarylalkene propeller molecules. NMR studies on 1 , for which this mechanism leads to a diastereomerization rather than an enantiomerization, gave a value of 79.5 kJ mol −1 for this process. After chromatographic separation of the enantiomers of 1 , it was also possible to determine the activation enthalpy of its enantiomerization, which presumably occurs by a [β,β′] two‐ring flip: 92.7 kJ mol −1 .