Graham Smith, D. Wen, R. C. Bott
Jul 6, 2001
Citations
3
Influential Citations
32
Citations
Journal
Australian Journal of Chemistry
Abstract
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).