Résumé
Hydrolyses of HCCSO3SiMe3 (1) and CH3CCSO3SiMe3 (2) lead to the formation of acetylenic sulfonic acids HCCSO3H·2.33H2O (3) and CH3CCSO3H·1.88H2O (4). These acids were reacted with guanidinium carbonate to yield [+C(NH2)3][HCCSO3] (5) and [+C(NH2)3][CH3CCSO3] (6). Compounds 1–6 were characterized by spectroscopic methods, and the X-ray crystal structures of the guanidinium salts were determined. The X-ray results of 5 show that the guanidinium cations and organosulfonate anions associate into 1D ribbons through R22(8) dimer interactions, whereas association of these ions in 6 is achieved through R22(8) and R12(6) interactions. The ribbons in 5 associate into 2D sheets through R22(8) dimer interactions and R36(12) rings, whereas those in 6 are connected through R12(6) and R22(8) dimer interactions and R46(14) rings. Compound 6 exhibits a single-layer stacking motif similar to that found in guanidinium alkane- and arenesulfonates, that is, the alkynyl groups alternate orientation from one ribbon to the next. The stacking motif in 5 is also single-layer, but due to interlayer hydrogen bonding between sulfonate anions, the alkynyl groups of each sheet all point to the same side of the sheet.