Interactions of Aromatic Carboxylic Acids with 8-Aminoquinoline: Synthesis and the Crystal Structures of the Proton-Transfer Compounds of 8-Aminoquinoline with Nitro-Substituted Benzoic Acids
Graham Smith, Graham Smith, Graham Smith, Urs D. Wermuth, Urs D. Wermuth, Urs D. Wermuth, Raymond Bott, Raymond C. Bott, Raymond C. Bott, Jonathan M. White, Jonathan M. White, Jonathan M. White, Anthony C. Willis, Anthony C. Willis and Anthony C. Willis
Australian Journal of Chemistry
54(3) 165 - 170
Proton-transfer compounds of 8-aminoquinoline with the nitro-substituted aromatic carboxylic acids 3-nitrobenzo-ic acid, [(C9H9N2+)(C7H4NO4–)] (1), 4-nitrobenzoic acid, [(C9H9N2+)(C7H4NO4–)(C7H5NO4)] (2), 3,5-dinitroben-zoic acid, [(C9H9N2+)(C7H3N2O6–)] (3), 5-nitrosalicylic acid, [(C9H9N2+)(C7H4NO5–)] (4) and 3,5-dinitrosalicylic acid, [(C9H9N2+)(C7H3N2O7–)] (5) have been prepared and characterized by using both infrared spectroscopy and single-crystal X-ray diffraction methods [(1) (4) and (5)]. In all compounds, protonation of the quinoline nitrogen occurs together with primary hydrogen-bonding interactions involving this group and the carboxylate group of the acid, while further peripheral associations result predominantly in simple chain polymeric structures. The attempted preparation of the adduct with 2,4,6-trinitrobenzoic acid gave the unstable, neutral, essentially 1 : 1 adduct with the decarboxylation product 1,3,5-trinitrobenzene, the X-ray crystal structure of which indicates the stoichiometry [(C9H8N2) 0.6 (C6H3N3O6)0.8] (6).
Full text doi:10.1071/CH01010
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