
TY  - JOUR
A1  - Smith, Graham 
A1  - Wermuth, Urs D. 
A1  - White, Jonathan M. 
T1  - Interactions of Aromatic Carboxylic Acids with Quinolin-8-ol (Oxine): Synthesis and the Crystal Structures of the Proton-Transfer Compounds with the Nitro-Substituted Benzoic Acids
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2001
VL  - 54
IS  - 3
SP  - 171
EP  - 175
KW  - 
UR  - https://doi.org/10.1071/CH01011 
N2  - Proton-transfer compounds of quinolin-8-ol (oxine) with the nitro-substituted aromatic carboxylic acids 2-nitrobenzoic acid, &#91;(C9H8NO+)(C7H4NO4&#8211;)&#183;H2O&#93; (1), 3-nitrobenzoic acid, &#91;(C9H8NO+)(C7H4NO4)&#8211;&#93; (2), 4-nitrobenzoic acid, &#91;(C9H8NO+)(C7H4NO4&#8211;)(C7H5NO4)&#93; (3), 3,5-dinitrobenzoic acid, &#91;(C9H8NO+)2(C7H3N2O6&#8211;)2&#183;3H2O&#93; (4), 5-nitrosalicylic acid, &#91;(C9H8NO+) (C7H4NO5&#8211;)&#93; (5) and 3,5-dinitrosalicylic acid, &#91;(C9H8NO+)(C7H3N2O7&#8211;)&#93; (6) have been prepared and characterized by using both infrared spectroscopy and single-crystal X-ray diffraction methods &#91;(3), (4) and (6)&#93;. 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, in the case of the trihydrate (4), also involving the water molecules, result predominantly in simple chain polymeric structures. 
ER  -

