Herein, we investigate the solid-state structure of N,N′-diarylbenzamidines in their neutral and cation states. Depending on the conditions, all three possible conformations were observed. Specifically, the E/Z form was observed in the neutral state, the sterically unfavorable Z/Z form was commonly observed in the halide salts, and the E/E form was dominant in the carboxylate salts because of the discrete salt bridge formation. The rigid H-shaped structure of the E/E form of bis(N,N′-diaryl)benzdiamidine created highly solvated crystals combined with carboxylic acids.
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Koichi Kodama
Azusa Miyazaki
Takuji Hirose
Crystal Growth & Design
Saitama University
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Kodama et al. (Tue,) studied this question.
www.synapsesocial.com/papers/69d893eb6c1944d70ce04d61 — DOI: https://doi.org/10.1021/acs.cgd.6c00064