Substituent influences on the keto-enol tautomerism in 1-(2-hydroxyphenyl)-3-alpha- and -beta-naphthylpropane-1,3-diones monitored by H-1 and C-13 NMR spectroscopy

Authors
Jios, JL Duddeck, H
Citation
Jl. Jios et H. Duddeck, Substituent influences on the keto-enol tautomerism in 1-(2-hydroxyphenyl)-3-alpha- and -beta-naphthylpropane-1,3-diones monitored by H-1 and C-13 NMR spectroscopy, Z NATURFO B, 55(2), 2000, pp. 193-202
Citations number
28
Categorie Soggetti
Chemistry
Journal title
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
ISSN journal
09320776 → ACNP
Volume
55
Issue
2
Year of publication
2000
Pages
193 - 202
Database
ISI
SICI code
0932-0776(200002)55:2<193:SIOTKT>2.0.ZU;2-4
Abstract
Synthesis of 18 1-(2-hydroxyphenyl)-3-alpha- and -beta-naphthylpropan-1,3-d iones is described. Their H-1 and C-13 NMR spectra were completely and unam biguously assigned using a combination of both homo- and heteronuclear (gs- COSY), H-1-detected heteronuclear one-bond (gs-HMQC) and long-range (gs-HMB C) correlation experiments. Substituent and conformation effects on the tau tomeric equilibria were identified and interpreted in terms of steric and e lectronic contributions.