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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)

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