Journal of the Chemical Society. Perkin transactions II p. 2209 - 2216 (1993)
Update date:2022-08-28
Topics:
Sharma, C. V. Krishnamohan
Panneerselvam, Kaliyamoorthy
Pilati, Tullio
Desiraju, Gautam R.
The crystal structure of the 1:1 donor-acceptor complex of 3,5-dinitrobenzoic acid and 4-(N,N-dimethylamino)benzoic acid contains the uncommon O-H...O hydrogen-bonded carboxy homodimers rather than the heterodimers found in nine other related complexes.The formation of these homodimers contradicts the general principle that in hydrogen-bonded networks, the strongest proton donor hydrogen bonds to the strongest proton acceptor.This unusual homodimer is obtained because of difficulties in C-H...O hydrogen bond formation, the consequent importance of ?...? stacking interactions and the enhanced stability of homodimer stacks over heterodimer stacks.Additionally, it is concluded that: (i) O-H...O hydrogen bonds can act as a conduit for charge transfer and may alter the polarization of atoms; (ii) C-H...O bonds can be used for molecular recognition and C-H...O patterns are sensitive to molecular stoichiometry and substituent positioning; (iii) stacking interactions influence the nature of hydrogen bonding and vice versa.This study shows that for precise supramolecular construction, strong and weak intermolecular interactions must be considered together.
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