The structures of eleven (4-phenyl)piperazinium salts containing organic anions

Archana, S. D. and Kiran Kumar, H. and Yathirajan, H. S. and Foro, Sabine and Butcher, Ray J. (2022) The structures of eleven (4-phenyl)piperazinium salts containing organic anions. Acta Crystallographica Section E, 78 (10). pp. 1016-1027. ISSN 2056-9890

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Eleven (4-phen­yl)piperazinium salts containing organic anions have been prepared and structurally characterized, namely, 4-phenyl­piperazin-1-ium 4-fluoro­benzoate monohydrate, C10H15N2+·C7H4FO2−·H2O, 1; 4-phenyl­piperazin-1-ium 4-bromo­benzoate monohydrate, C10H15N2+·C7H4BrO2−·H2O, 3; 4-phenyl­piperazin-1-ium 4-iodo­benzoate, C10H15N2+·C7H4IO2−, 4; 4-phenyl­piperazin-1-ium 4-nitro­benzoate, C10H15N2+·C7H4NO4−, 5; 4-phenyl­piperazin-1-ium 3,5-di­nitro­salicylate, C10H15N2+·C7H3N2O7−, 6; 4-phenyl­piperazin-1-ium 3,5-di­nitro­benzoate, C10H15N2+·C7H3N2O6−, 7; 4-phenyl­piperazin-1-ium picrate, C10H15N2+·C6H2N3O7−, 8; 4-phenyl­piperazin-1-ium benzoate monohydrate, C10H15N2+·C7H5O2−·H2O, 9; 4-phenyl­piperazin-1-ium p-toluene­sulfonate, C10H15N2+·C7H7O3S−, 10; 4-phenyl­piperazin-1-ium tartarate monohydrate, C10H15N2+·C4H5O6−·H2O, 11; and 4-phenyl­piperazin-1-ium fumarate, C10H15N2+·C4H3O4−, 12. Compounds 1 and 3–12 are all 1:1 salts with the acid proton transferred to the phenyl­piperaizine basic N atom (the secondary amine) with the exception of 3 where there is disorder in the proton position with it being 68% attached to the base and 32% attached to the acid. Of the structures with similar stoichiometries only 3 and 9 are isomorphous. The 4-phenyl substituent in all cases occupies an equatorial position except for 12 where it is in an axial position. The crystal chosen for structure 7 was refined as a non-merohedral twin. There is disorder in 5, 6, 10 and 11. For both 5 and 6, a nitro group is disordered and was modeled with two equivalent orientations with occupancies of 0.62 (3)/0.38 (3) and 0.690 (11)/0.310 (11), respectively. For 6, 10 and 11, this disorder is associated with the phenyl ring of the phenyl­piperazinium cation with occupancies of 0.687 (10)/0.313 (10), 0.51 (7)/0.49 (7) and 0.611 (13)/389 (13), respectively. For all salts, the packing is dominated by the N—H⋯O hydrogen bonds formed by the cation and anion. In addition, several structures contain C—H⋯π (1, 3, 4, 8, 9, 10, and 12) and aromatic π–π stacking inter­actions (6 and 8) and one structure (5) contains a –NO2⋯π inter­action. For all structures, the Hirshfeld surface fingerprint plots show the expected prominent spikes as a result of the N—H⋯O and O—H⋯O hydrogen bonds.

Item Type: Article
Uncontrolled Keywords: crystal structure, phenylpiperazinium cation, organic salt
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 01 Oct 2022 05:33
Last Modified: 01 Oct 2022 05:33

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