Synthesis and characterization of two organic cation hydrogensulfates: 1-(2,5-dimethylphenyl)piperazine-1,4-diium bis(hydrogensulfate) monohydrate (SI) and 1-(2,3-dimethylphenyl)piperazine-1,4-diium bis(hydrogensulfate) (SII)

• Published in: Journal of molecular structure Vol. 1134; pp. 625 - 637
• Main Authors: Arbi, M., Khedhiri, L., Wojtaś, M., Jeanneau, E., Lefebvre, F., Ben Nasr, C.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.04.2017
• Subjects: CP-MAS NMR; Crystal structure; Infrared spectroscopy; Thermal analysis; X-ray diffraction; X-ray diffraction; Infrared spectroscopy; Thermal analysis; CP-MAS NMR; Crystal structure
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2016.12.099

Treatment of 1-(2,5-dimethylphenyl)piperazine and 1-(2,3-dimethylphenyl)piperazine with H2SO4 in 2:1 molar ratio at RT affords the corresponding sulfate salts [C12H20N2][HSO4]2·H2O (SI) and [C12H20N2][HSO4]2 (SII). These compounds have been characterized by X-ray diffraction, thermal analysis and spectroscopic investigations (IR and NMR). In the atomic arrangement of (SI) the HSO4− anions are associated by pairs linked to the water molecules forming corrugated ribbons, while in the (SII) structure, the pairs of the HSO4− anions form corrugated chains. Solid-state 13C and 15N CP-MAS NMR spectroscopies are in agreement with the X-ray structure. The vibrational absorption bands were identified by infrared spectroscopy. NMR peaks were attributed with the aid of DFT calculations. The electronic properties such as HOMO and LUMO energies were determined. [Display omitted] •Two new organic cation hydrogensulfates, [C12H20N2][HSO4]2·H2O (SI) and [C12H20N2][HSO4]2 (SII), were synthesized.•Solid-state 13C and 15N CP-MAS NMR spectroscopies are in agreement with the X-ray structure.•NMR peaks were attributed with the aid of DFT calculations.•The electronic properties such as HOMO and LUMO energies were determined.•These materials were also investigated by TGA and DTA.