ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Hydrogen bonding in phenols. IX. Synthesis of the OH ... π intramolecular hydrogen bonding of alkyl-substituted 2-hydroxydiphenylmethanes

A. Kanala and Š. Kováč

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava

Abstract: The synthesis of 2-hydroxy-X'-diphenylmethanes, where X ' = H, 4-СНз, 4-C₂H₅, 4-CH(CH₃)₂, 4-С(СН₃)_з. 2,4,6-tri(CH₃), 2,3,5,6-tetra(CH₃), 2,3,4,5,6-penta(CH₃), is described. The OH...π intramolecular hydrogen bonding of the above-mentioned compounds in CCI₄ solution is studied by infrared spectroscopy. Energies of the hydrogen bonding were found to increase with the increasing number of alkyl groups on the aromatic ring and they linearly correlate with the ionization potentials of the appropriate alkyl benzenes.

Full paper in Portable Document Format: 292a215.pdf

Chemical Papers 29 (2) 215–218 (1975)