Intra- and intermolecular hydrogen bondings in steroids - A combined experimental and theoretical study

Magyar, A. and Szendi, Z. and Kiss T., János and Pálinkó, István (2003) Intra- and intermolecular hydrogen bondings in steroids - A combined experimental and theoretical study. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 666-67. pp. 163-168. ISSN 0166-1280

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Abstract

FTIR measurements on the solutions of previously not studied steroids [(20R)[6'(3,4'[2 H]-dihydropyranyl)]-pregn-5-ene-3beta,20-diol 3(2"-tetrahydropyranyl) ether (1) and (20R)[6'(3,4'[2'H]-dihydropyranyl)]-pregn-5-ene-3beta,20-diol 3-acetate (2)] with varying concentrations revealed, that intra- as well as intermolecular interactions existed for both molecules. The former was more important for compound 1 and the latter for compound 2. Only intermolecular hydrogen bonds were found in the crystalline state, however. Molecular modeling (PM3 code) allowed a fair estimation of intramolecular hydrogen bonding parameters and helped in suggesting possible arrangement for compound 2 in solution.

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