Hydrogen bonding in proton-transfer compounds of 5-sulfosalicylic acid with bicyclic heteroaromatic Lewis bases.

Abstract

The crystal structures of quinolinium 3-carboxy-4-hydroxy­benzene­sulfonate trihydrate, C9H8N+·C7H5O6S−·3H2O, (I), 8-hydroxy­quinolinium 3-carboxy-4-hydroxy­benzene­sulfonate monohydrate, C9H8NO+·C7H5O6S−·H2O, (II), 8-amino­quinolinium 3-carboxy-4-hydroxy­benzene­sulfonate dihydrate, C9H9N2+·C7H5O6S−·2H2O, (III), and 2-carboxy­quinolinium 3-carboxy-4-hydroxy­benzene­sulfonate quinolinium-2-carboxylate, C10H8NO2+·C7H5O6S−·C10H7NO2, (IV), four proton-transfer compounds of 5-sulfosalicylic acid with bicyclic heteroaromatic Lewis bases, reveal in each the presence of variously hydrogen-bonded polymers. In only one of these compounds, viz. (II), is the protonated quinolinium group involved in a direct primary N+—H⋯O(sulfonate) hydrogen-bonding interaction, while in the other hydrates, viz. (I) and (III), the water mol­ecules participate in the primary intermediate interaction. The quinaldic acid (quinoline-2-carboxylic acid) adduct, (IV), exhibits cation–cation and anion–adduct hydrogen bonding but no direct formal heteromolecular interaction other than a number of weak cation–anion and cation–adduct π–π stacking associations. In all other compounds, secondary interactions give rise to network polymer structures.