Topochemical bias in the hydrogen-bonded networks of guanidinium carboxybenzenesulfonates

Abstract

Herein we describe the changes in the packing patterns and discuss the structural modifications in guanidinium carboxybenzenesulfonates G·CBS [C(NH₂)₃]⁺[XC₆H₄SO₃]⁻ (where X is the carboxylic group) compared with those in guanidinium benzenesulfonate G·BS. Generally, the one-dimensional arrangements in all three crystals comprise the same ribbon formations. However, the further organization of the ribbons is significantly different in G·CBS. We analyse the donor and acceptor efficacy of the additional functional group to disrupt some of the basic hydrogen bonds between the guanidinium and the sulfonium portions in G·BS. Since the carboxylic group introduces a mismatching of the sites on the counter ions, the changes in the symmetry relations essentially depend upon the topology of the substituent X, which results in modified packing patterns. All engineering peculiarities are analysed with respect to the symmetry constraints and geometrical demands of the packing forces.