Structure of dilignol,?-O-4-[1-(4-hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol] in crystal and in solution

Autor: S. M. Shevchenko, Yu. K. Yakobsons, M. G. Liepin'sh, A. F. Mishnev
Rok vydání: 1990
Předmět:
Zdroj: Journal of Structural Chemistry. 30:809-814
ISSN: 1573-8779
0022-4766
DOI: 10.1007/bf00763807
Popis: The structure of dilignol, 1-(4-hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol was studied by x-ray diffraction structural analysis and1H PMR spectroscopy. The dilignol molecules crystallize in an extended conformation with trans-Ar-C-C-O and trans-C-C-O-Ar structures: the angle between the plane of the aromatic systems was 74.0°. This conformation was stabilized by intermolecular hydrogen bonds, which linked the molecules into chains. Weak Y-shaped hydrogen bonds were found between molecules of adjacent chains. These results were compared with the literature data on the crystal structure of β-O-4 dilignols. A similar conformation of dilignol stabilized by an intramolecular hydrogen bond, whose existence was indicated by IR spectroscopy, was found to predominate in acetone and chloroform solutions. A conclusion was drawn concerning the conformational mobility of β-O-4 dilignols and the factors determining the conformational composition of dilignols in solution were discussed.
Databáze: OpenAIRE
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