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The conformational isomerism and stereoelectronic interactions present in 2'-haloflavonols were computationally analyzed. On the basis of the quantum theory of atoms in molecules (QTAIM) and natural bond orbital (NBO) analysis, the conformer stabilities of 2'-haloflavonols were found to be dictated mainly by a C=O···H-O intramolecular hydrogen bond, but an unusual C-F···H-O hydrogen-bond and intramolecular C-X···O nonbonding interactions are also present in such compounds.

Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols