Hydrogen bonds, tautomers, and conformation in 2-hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl ketone

被引：8
|
作者：
Echeverría, GA
Jios, JL
Autino, JC
Punte, G
机构：
[1] Natl Univ La Plata, Fac Ciencias Exactas, IFLP, RA-1900 La Plata, Argentina
[2] Natl Univ La Plata, Fac Ciencias Exactas, Dept Fis, LANADI, RA-1900 La Plata, Argentina
[3] Natl Univ La Plata, Fac Ingn, Dept Fisicomatemat, RA-1900 La Plata, Argentina
[4] Natl Univ La Plata, Fac Ciencias Exactas, Dept Quim, LADECOR, RA-1900 La Plata, Argentina
来源：
STRUCTURAL CHEMISTRY | 2000年 / 11卷 / 06期
关键词：
keto-enol tautomerism; single crystal X-ray diffraction; intra- and intermolecular hydrogen bond; resonance-assisted hydrogen bonds; IR data;
D O I：
10.1023/A:1026522105977
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Single crystal X-ray diffraction and IR spectroscopy have been used to study the conformation of 2-hydroxyphenyl 2-hydroxy-2-(alpha -naphthyl)vinyl ketone in solid state. It was found that one of the two possible enol tautomeric forms is stabilized in the crystal. The 1-hydroxy-3-oxo-1,3-propenylene moiety. O=C-CH=C-OH, shows a strong intramolecular H bond with a definite character of reasonance-assisted hydrogen bond in spite of being in competition with ring intermolecular hydrogen bonds. The comparison of the present results with solution NMR data indicates that the molecular geometry in solid state and in solution are similar.
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页码：367 / 373
页数：7
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