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Isolation of an Acid/Base Complex in Solution Puts the Brakes on Nitrogen Inversion
Author(s) -
Wash Paul L.,
Renslo Adam R.,
Rebek, Jr. Julius
Publication year - 2001
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(20010401)40:7<1221::aid-anie1221>3.0.co;2-n
Subject(s) - cavitand , inversion (geology) , nitrogen , hydrogen bond , chemistry , molecule , nitrogen inversion , chemical physics , computational chemistry , organic chemistry , supramolecular chemistry , biology , paleontology , structural basin
An introverted carboxy functionality of the cavitand shown, significantly alters the dynamics of nitrogen inversion of guest molecules, as well as the hydrogen bonding and guest tumbling in the inner recess. For example, NMR experiments indicate that N‐inversion of ethylmethylisopropylamine is several orders of magnitude slower in the cavitand than the rate observed in solution.