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Revision of the structure and stereochemistry of the 2‐naphthol–acetaldehyde 2:2 condensation product. A study by X‐ray crystallography and the AM1 method
Author(s) -
RashidiRanjbar Parviz,
Mohajeri Ali,
Hossein Mahmoudkhani Amir
Publication year - 2001
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.355
Subject(s) - chemistry , intramolecular force , crystal structure , molecule , hydrogen bond , acetaldehyde , condensation , solid state , crystallography , stacking , stereochemistry , x ray , organic chemistry , ethanol , physics , thermodynamics , quantum mechanics
The structure of the 2:2 condensation product of 2‐naphthol and acetaldehyde, 1‐(1‐methyl‐2,3‐dihydro‐1 H ‐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.