Guanidinium Alkynesulfonates with Single-Layer Stacking Motif: Interlayer Hydrogen Bonding Between Sulfonate Anions Changes the Orientation of the Organosulfonate R Group from “Alternate Side” to “Same Side”
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.
Domaines
Chimie organique
Origine : Fichiers produits par l'(les) auteur(s)
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