CONFORMATION AND ROTATION BARRIERS OF SUB STITUTED GLYOXYLIC-ACID AMIDES

Authors
SPAETH M PLISCHKA P BOHNEN FM HERBSTIRMER R LAATSCH H
Citation
M. Spaeth et al., CONFORMATION AND ROTATION BARRIERS OF SUB STITUTED GLYOXYLIC-ACID AMIDES, Journal fur praktische Chemie, Chemiker-Zeitung, 339(3), 1997, pp. 243-249
Citations number
27
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
339
Issue
3
Year of publication
1997
Pages
243 - 249
Database
ISI
SICI code
0941-1216(1997)339:3<243:CARBOS>2.0.ZU;2-I
Abstract
Semiempirical calculations predict an orthogonal orientation of the ca rbonyl groups in tertiary glyoxylic acid amides, which is in good agre ement with an X-ray structure analysis of 5. Due to the influence of t he a-carbonyl group, the rotation barrier in the substituted glyoxylic acid amides 2a-d, 3a, 3b, and 4-6 (Delta G(c)(#)=84-92 kJ mol(-1)) is about 10 kJ/mol higher than in simple acid amides, as was found by dy namic NMR line shape analysis.