Mechanism of formation of chiral crystals studied by using induced-chiral molecule as a probe

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Tartornic acid, phenylmaronic acid and chloronitrobenzoic acid have been undertaken as model compounds in order to investigate the mechanism of formation of chiral crystals which are composed of achiral molecules. The acidic anions of the first two compounds are optically active. The last one has an axial-chirality when it is crystallized. We have prepared salts or intermolecular compounds of the above compounds with amine, pyridine and amino acid derivatives, and determined the crystal structures by single crystal X-ray diffraction. Furthermore, we have determined crystal structures of salts or intermolecular compounds of chloranilic acid with amine, pyridine and amino acid derivatives in order to investigate their hydrogen bond scheme and the proton transfer mechanism in the hydrogen bond.Part of the results have already been published in the international crystallographic journals. The published crystal structures are: (1) 2-pyridone-tartronic acid (1/1), 3-hydroxypyridinium hydrogen tartronate and 4-hydroxypyridinium hydrogen tartronate; (2) benzimidazolium hydrogen phenylmalonate; (3) 3,5-lutidinium-2-chloro-4-nitrobenzoate-2-chloro-4-nitrobenzoic acid (1/1/1), 3-cyanopyridine-2-chloro-4-nitrobenzoic acid (1/1); (4) chloranilate with carboxypyridinium, cytosinium, phenazine, picolinium, piperidinium, pyrrolidinium, methylpyrazolium, tetrahydroquinolinium and trimethylpyridinium ion.