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Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols
Author(s) -
Mammino Liliana,
Kabanda Mwadham M.
Publication year - 2011
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.23280
Subject(s) - intramolecular force , chemistry , hydrogen bond , polarizable continuum model , phloroglucinol , acetonitrile , computational chemistry , chloroform , solvent , solvent effects , derivative (finance) , polarizability , molecule , stereochemistry , organic chemistry , financial economics , economics
Acylphloroglucinols (ACPLs) are polyphenolic compounds derivative from phloroglucinol, characterized by the presence of at least one COR group and exhibiting a variety of biological activities, which makes them interesting for drug development possibilities. This study investigates patterns in the ways in which weaker intramolecular hydrogen bonds contribute to their conformational stabilization, considering the CH···O H‐bonds, present in all ACPLs, and the OH···π H‐bonds, present in ACPLs in which one or more substituents contain a π bond or system sufficiently close to a phenol OH for the H‐bond to be possible. The results in vacuo and in three different solvents (chloroform, acetonitrile, and water) show that, whereas CH···O plays a significant roles in all these media, the role of OH···π decreases with increasing solvent polarity. Calculations in vacuo are performed at various levels to enable performance comparisons; calculations in solution use the polarizable continuum model. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2011