P. Rashidi-Ranjbar, A. Mohajeri, A. Mahmoudkhani
Apr 1, 2001
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Journal
Journal of Physical Organic Chemistry
Abstract
The structure of the 2:2 condensation product of 2-naphthol and acetaldehyde, 1-(1-methyl-2,3-dihydro-1H-benzo[ f ]chromen-3-yl)-2-naphthol, revised by X-ray crystallography, is presented. A moderate intramolecular hydrogen bond is found between the phenolic OH and chromene oxygen atom both in the solid state and in solution. In the crystal structure, the naphthyl groups are oriented in parallel with a π–π stacking distance of 354 pm. AM1 studies are used to explain the formation of one of the four possible stereoisomers for the title compound. Comparison of the experimental and calculated coupling constants indicates that the molecule adopts exclusively the solid-state structure in solution. Copyright © 2001 John Wiley & Sons, Ltd.