Syntheses and crystal structures of 4-(4-nitrophenyl)piperazin-1-ium benzoate monohydrate and 4-(4-nitrophenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate

Prasad, Holehundi J. Shankara; Devaraju,; Vinaya,; Yathirajan, H. S.; Parkin, Sean; Glidewell, Christopher

doi:10.1107/s2056989022007472

Cited by 4 publications

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References 30 publications

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“…Among them, a potential application for 4-nitrophenylpiperazine (NPP) can be indicated (Ko ¨nig et al, 1997;Lu, 2007;Wang et al, 2014). We have recently reported the crystal structures of eight salts of 4-nitrophenylpiperazine (Mahesha et al, 2022;Shankara Prasad et al, 2022). In view of the importance of piperazines in general and the use of 4nitrophenylpiperazine in particular, the present article reports the synthesis, crystal structure and Hirshfeld surface analysis of two salts of 4-nitrophenylpiperazine with organic acids, namely, 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate, C 12 H 14 F 3 N 3 O 4 , (I) and 4-(4-nitropheny)piperazin-1-ium trichloroacetate, C 12 H 14 Cl 3 N 3 O 4 , (II).…”

Section: Chemical Contextmentioning

confidence: 99%

Syntheses, crystal structures and Hirshfeld surface analysis of 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate and 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate

Prasad¹,

Devaraju²,

Murthy³

et al. 2023

Acta Cryst E

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The synthesis and crystal structures of the molecular salts of 4-(4-nitrophenyl)piperazine with trifluoroacetate, namely, 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate, C10H14N3O2 +·C2F3O2 − (I), and with trichloroacetate, namely, 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate, C10H14N3O2 +·C2Cl3O2 −, (II), are reported and compared. A partial positional disorder of the anions was found. In both structures, the piperazine rings adopt a chair conformation, whereas the positions of the nitrophenyl group on the piperazine ring differ from bisectional in (I) to equatorial in (II). In both structures, the supramolecular assemblies are mono-periodic on the basis of the chain-of-rings motifs supported by aromatic π–π interactions. Hirshfeld surface analysis was used to explore the intermolecular close contacts in both crystals. The most dominant contacts of the Hirshfeld surface of the cation–anion pairs of the asymmetric units are O...H/H...O, and those with a contribution of halogen atoms: F...H/H...F in (I) and Cl...H/H...Cl in (II), respectively.

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Section: Chemical Contextmentioning

confidence: 99%

Syntheses, crystal structures and Hirshfeld surface analysis of 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate and 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate

Prasad¹,

Devaraju²,

Murthy³

et al. 2023

Acta Cryst E

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“…The phenyl rings in adjacent cations forminteractions with a perpendicular distance between centroids of 3.586 (4) A ˚(symmetry code: Àx, 1 À y, Àz; slippage = 0.379 A ˚). 2-carboxy-4,6-dinitrophenolate (BEFGOM) have been reported (Shankara Prasad et al, 2022). A survey of these published derivatives containing the 4-(4-nitrophenyl)piperazin-1-ium cation shows that the most common conformation adopted by the 4-nitrophenyl substituent with respect to the six-membered piperazinium ring is equatorial (LUDMUU, NEBVOJ, NEBVUP, NEBWAW, NEBWEA, NEBWOK, BEFGIG and BEYRIK) with only three adopting the axial conformation (LUDMUU, BEFGOM, and BEYREG).…”

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confidence: 99%

Syntheses and crystal structures of three salts of 1-(4-nitrophenyl)piperazine

Prasad¹,

Devaraju²,

Yathirajan³

et al. 2023

Acta Cryst E

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The crystal structures and Hirshfeld surface analyses of three salts of 1-(4-nitrophenyl)piperazine with 2-chlorobenzoic acid, 2-bromobenzoic acid and 2-iodobenzoic acid are reported. The chlorobenzoate salt, C10H14N3O2 +·C7H4ClO2 −, contains whole-ion-disordered cations and anions, which were modeled with two equivalent conformations with occupancies of 0.745 (10)/0.255 (10) and 0.563 (13)/0.437 (13), respectively. The bromobenzoate and iodobenzoate derivatives are isomorphous and crystallize as hemihydrates, viz. C10H14N3O2 +·C7H4BrO2 −·0.5H2O and C10H14N3O2 +·C7H4IO2 −·0.5H2O, respectively [the water molecule is disordered over two locations with occupancies of 0.276 (3)/0.223 (3) for the iodobenzoate derivative]. In the extended structures, all three salts feature an R 4 4(12) loop of two anions and two cations linked by N—H...O hydrogen bonds.

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Syntheses and crystal structures of four 4-(4-nitrophenyl)piperazinium salts with hydrogen succinate, 4-aminobenzoate, 2-(4-chlorophenyl)acetate and 2,3,4,5,6-pentafluorobenzoate anions

et al. 2023

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The syntheses and crystal structures are presented for four organic salts of the 4-(4-nitrophenyl)piperazinium cation, namely, 4-(4-nitrophenyl)piperazinium hydrogen succinate, C10H14N3O2 +·C4H5O4 − (I), 4-(4-nitrophenyl)piperazinium 4-aminobenzoate monohydrate, C10H14N3O2 +·C7H6NO2 −·H2O (II), 4-(4-nitrophenyl)piperazinium 2-(4-chlorophenyl)acetate, C10H14N3O2 +·C8H6ClO2 − (III) and 4-(4-nitrophenyl)piperazinium 2,3,4,5,6-pentafluorobenzoate, C10H14N3O2 +·C7F5O2 − (IV). The salts form from mixtures of N-(4-nitrophenyl)piperazine and the corresponding acid [succinic acid (I), 4-aminobenzoic acid (II), 2-(4-chlorophenyl)acetic acid (III) and 2,3,4,5,6-pentafluorobenzoic acid (IV)] in mixed solvents of methanol and ethyl acetate. Salts I, III, and IV are anhydrous, whereas II is a monohydrate. In each structure, the overall conformation of the cation is determined by the disposition of the exocyclic N—C bond of the piperazine ring (either axial or equatorial) and twists about the N—C bond between the piperazine ring and its attached 4-nitrophenyl ring. The packing motifs in each structure are quite different, though all are dominated by strong N—H...O hydrogen bonds, which are augmented in I and II by O—H...O hydrogen bonds, and in III by a π–π stacking interaction between inversion-related 4-nitrophenyl groups.

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Syntheses and crystal structures of 4-(4-nitrophenyl)piperazin-1-ium benzoate monohydrate and 4-(4-nitrophenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate

Cited by 4 publications

References 30 publications

Syntheses, crystal structures and Hirshfeld surface analysis of 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate and 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate

Syntheses, crystal structures and Hirshfeld surface analysis of 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate and 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate

Syntheses and crystal structures of three salts of 1-(4-nitrophenyl)piperazine

Syntheses and crystal structures of four 4-(4-nitrophenyl)piperazinium salts with hydrogen succinate, 4-aminobenzoate, 2-(4-chlorophenyl)acetate and 2,3,4,5,6-pentafluorobenzoate anions

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