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

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroqui noline and 5-nitroiso quinoline 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 compoun ds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7 NO2)(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 [(C7H7NO2 )(C9H6N2O2)]. Other compounds described are the (1:1) adducts of 4-ami nobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network as sociations while in none of the examples is any proton transfer involv ed.