Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes

Abstract

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C₇H₇NO₂)(C₉H₆N₂O₂)], 4-aminobenzoic acid with 5-nitroquinoline [(C₇H₇NO₂)₂(C₉H₆N₂O₂)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C₇H₇NO₂)(C₉H₆N₂O₂)] and 4-aminobenzoic acid with 5-nitroisoquinoline [(C₇H₇N₂O₂)(C₉H₆N₂O₂)]. Other compounds described are the (1 : 1) adducts of 4-aminobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network associations while in none of the examples is any proton transfer involved.