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Quantifying Homo‐ and Heteromolecular Hydrogen Bonds as a Guide for Adduct Formation
Author(s) -
Delori Amit,
Galek Peter T. A.,
Pidcock Elna,
Jones William
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103129
Subject(s) - hydrogen bond , chemistry , adduct , crystallography , medicinal chemistry , molecule , organic chemistry
Abstract An investigation into the predictability of molecular adduct formation is presented by using the approach of hydrogen bond propensity. Along with the predictions, crystallisation reactions ( 1a – 1j ) were carried out between the anti‐malarial drug pyrimethamine ( 1 ) and the acids oxalic ( a ), malonic ( b ), acetylenedicarboxylic ( c ), adipic ( d ), pimelic ( e ), suberic ( f ), azelaic acids ( g ), as well as hexachlorobenzene ( h ), 1,4‐diiodobenzene ( i ), and 1,4‐diiodotetrafluorobenzene ( j ); seven ( 1a to 1g ) of these successfully formed salts. Five of these seven salts were found to be either hydrated or solvated. Hydrogen bond propensity calculations predict that hydrogen bonds between 1 and acids a – g are more likely to form rather than the H bonds involved in self‐association, providing a rationale for the observation of the seven new salts. In contrast, propensity of hydrogen bonds between 1 and h – j is much smaller as compared to other bonds predicted for self‐association/solvate formation, in agreement with the observed unsuccessful reactions.