NMR Studies of Drugs: Antipyrine and Analogs. II.1H and13C Chemical Shift Dispersion as Conformation Indicator for theN-Phenyl Ring.
作者:
KunisiS. Venkatasubban,
Robert Rothchild,
期刊:
Spectroscopy Letters
(Taylor Available online 1997)
卷期:
Volume 30,
issue 8
页码: 1685-1697
ISSN:0038-7010
年代: 1997
DOI:10.1080/00387019708006752
出版商: Taylor & Francis Group
关键词: Nuclear magnetic resonance;Steric hindrance;Conformational analysis;Conjugation;1, 2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
数据来源: Taylor
摘要:
A potentially useful simple method is proposed to determine whether theN-phenyl rings in the analgesic drug, antipyrine (and analogs), preferentially exist in a conformation which is approximately coplanar with, or is perpendicular to, the five-membered heterocyclic rings. The method is based on the magnitude of “spectral dispersion,” that is, the degree of NMR chemical shift differences for the proton and the protonated carbon signals of theN-phenyl. A narrow range of chemical shifts is considered suggestive of a preferred perpendicular conformation, which reduces mesomeric effects of conjugation and minimizes steric hindrance with nearby groups. Representative chemical shift data for model compounds are presented.
点击下载:
PDF (489KB)
返 回