Premium
The First Crystallographic Evidence for the Structures of ortho ‐Lithiated Aromatic Tertiary Amides
Author(s) -
Clayden Jonathan,
Davies Robert P.,
Hendy Mark A.,
Snaith, Ronald,
Wheatley Andrew E. H.
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<1238::aid-anie1238>3.0.co;2-g
Subject(s) - amide , ring (chemistry) , lithium (medication) , aromaticity , crystallography , crystal structure , chemistry , group (periodic table) , perpendicular , twist , stereochemistry , molecule , organic chemistry , geometry , mathematics , medicine , endocrinology
Despite the near‐perpendicular arrangement of the amide group and aromatic ring in many tertiary aromatic amides, ortho ‐lithiation is still a very straightforward process. The first X‐ray crystal structures of ortho ‐lithiated amides reveal why: the angle of twist is lessened to some degree, and the lithium ion lies far from the plane of the aromatic ring, with stabilization of the strained structure being achieved by dimerization (see scheme).