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Synthesis, Physicochemical Properties, and Conformational Studies of (3-Alkoxymethyl-4-hydroxyphenyl)ethanones

R. Čižmáriková, M. Polakovičová, and E. Mišíková

Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, SK-832 32 Bratislava



Received: 26 October 2001

Abstract: A homologous series of (3-alkoxymethyl-4-hydroxyphenyl)ethanones was prepared by the reaction of (3-chloromethyl-4-hydroxyphenyl)ethanone with the different alcohols in the presence of sodium hydrogen carbonate. The confirmation of structures was achieved by interpretation of IR, UV, and 1H NMR spectra. Molecular modeling methods were used to establish conformations with global and local energetic minima. It was found that energetically the most stable conformations involved hydrogen bond formation between the hydrogen of phenolic group and the oxygen of alkoxyl group. Enthalpy values of hydrogen bonds of selected compounds were 24.86—30.51 kJ mol−1 and their distances were in the range 0.282—0.293 nm.

Full paper in Portable Document Format: 564a256.pdf


Chemical Papers 56 (4) 256–260 (2002)

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