Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures

The reactions of equimolar amounts of alkyltriphenylphosphonium bromide with arenesulfonic acids in an aqueous-acetone solution afford alkyltriphenylphosphonium arenesulfonates [Ph₃PCH₂ОMe]-[OSO₂C₆H₃(OH-4)(COOH-3)] (I), [Ph₃PCH₂СN][OSO₂C₆H₄(COOH)-2] (II), [Ph₃PCH₂C(O)Me]-[OSO₂С₆H₄(COOH-2] (III), and [Ph₃PCH₂C(O)Me][OSO₂Naft-1] (IV). According to the X-ray diffraction (XRD) data, the crystals of compounds I−IV have ionic structures with tetrahedral alkyltriphenylphosphonium cations (P−С 1.7820(19)−1.8330(20) Å, CPC 105.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound I contains hydrogen bonds (S=O···H−OC(O) 1.87 Å) linking the arenesulfonate anions into chains. The structural organization of the crystals of compounds I−IV is mainly formed due to numerous weak hydrogen bonds between the cations and anions, for instance, S=O···H−C_Ar (2.29−2.70 Å), C=O∙∙∙H–C (2.48 and 2.59 Å), and N∙∙∙H–C (2.62−2.68 Å).