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DFT Calculations on a New Class of C 3 ‐Symmetric Organic Bases: Highly Basic Proton Sponges and Ligands for Very Small Metal Cations
Author(s) -
Bucher Götz
Publication year - 2003
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.200351648
Subject(s) - lone pair , quinoline , acetonitrile , chemistry , conjugate , borane , metal , proton , computational chemistry , medicinal chemistry , organic chemistry , molecule , physics , mathematics , catalysis , mathematical analysis , quantum mechanics
Back to bases : What happens, if three nitrogen lone pairs are forced to interact with each other? An extraordinary increase in basicity. This conclusion is the result of DFT calculations which, for example, predict a p K a value (of the conjugate acid, in acetonitrile) of 30.2 for tris(8‐quinolyl)borane 1 . The basicity is due to a strongly destabilizing interaction between the three quinoline lone pairs in the free bases.