Molecular recognition involving an interplay of O–H⋯O, C–H⋯O and π⋯π interactions. The anomalous crystal structure of the 1 : 1 complex 3,5-dinitrobenzoic acid–4-(N,N-dimethylamino)benzoic acid

• DOI: 10.1039/p29930002209
• Publication Date: 2004-04-27T11:41:24Z
• Authors: C. V. Krishnamoha...; Kaliyamoorthy Pan...; Tullio Pilati; Gautam R. Desiraju
• Keywords: Acceptor; Benzoic acid

The crystal structure of the 1:1 donor–acceptor complex 3,5-dinitrobenzoic acid and 4-(N,N-dimethylamino)benzoic contains uncommon O–H ⋯ O hydrogen-bonded carboxy homodimers rather than heterodimers found in nine other related complexes. formation these contradicts general principle that networks, strongest proton donor hydrogen bonds to acceptor. This unusual homodimer is obtained because difficulties C–H bond formation, consequent importance π⋯π stacking interactions enhanced stability stacks over heterodimer stacks. Additionally, it concluded that: (i) can act as a conduit for charge transfer may alter polarization atoms; (ii) be used molecular recognition patterns are sensitive stoichiometry substituent positioning; (iii) influence nature bonding vice versa. study shows precise supramolecular construction, strong weak intermolecular must considered together.