Crystal structure studies of 4-ethylpiperazin-1-ium 3,5-dinitrobenzoate, 4-methylpiperazin-1-ium 3,5-dinitrobenzoate and 4-methylpiperazin-1-ium 4-iodobenzoate

Archana, Sriramapura D; Kumar, Haruvegowda Kiran; Yathirajan, H. S.; Foro, Sabine; Abdelbaky, Mohammed S. M.; Garcı́a-Granda, Santiago

doi:10.1107/s2056989021010689

Cited by 4 publications

(2 citation statements)

References 34 publications

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“…NMR-based investigations of acyl-functionalized piperazines concerning their conformational behaviour in solution has been studied and the crystal structures of 1-(4-fluorobenzoyl)-4-(4-nitrophenyl)piperazine, 1-(4-bromobenzoyl)-4-(4-nitrophenyl)piperazine and 1-(3-bromobenzoyl)-4-(4-nitrophenyl)piperazine have been reported (Wodtke et al, 2018). We have recently reported the crystal structures of some salts of 4-methoxyphenylpiperazine (Kiran Kumar et al, 2019) and also 2-methoxyphenylpiperazine (Harish Chinthal et al, 2020), as well as some salts of piperazine derivatives (Archana et al, 2021).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of six 4-(4-nitrophenyl)piperazin-1-ium salts

Mahesha¹,

Kumar²,

Yathirajan³

et al. 2022

Acta Cryst E

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Six piperazinium salts, namely 4-(4-nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate, C10H14N3O2 +·C7H4BrO2 −·2H2O, (I), 4-(4-nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate, C10H14N3O2 +·C7H4IO2 −·2H2O, (II), 4-(4-nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate, C10H14N3O2 +·C7H5O3 −·H2O, (III), 4-(4-nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate, C10H14N3O2 +·C8H7O2 −·H2O, (IV), 4-(4-nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate, 2C10H14N3O2 +·2C8H7O3 −·H2O, (V), and 4-(4-nitrophenyl)piperazin-1-ium 4-ethoxybenzoate, 2C10H14N3O2 +·2C9H9O3 −, (VI), have been synthesized and their crystal structures solved by single-crystal X-ray diffraction, revealing that all of them crystallize in the triclinic space group P\overline{1} except for (V), which crystallizes in the monoclinic space group P21/c and has a disordered nitro group. Compounds (I) and (II) are isostructural. The crystal packing of (I)–(V) is constructed from organic chains formed by a combination of hydrogen bonds of type N—H...O and/or O—H...O and other weak interactions of type C—H...O and/or C—H...π, forming sheets, whereas (VI) shows a cationic and anionic-based layer structure.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of six 4-(4-nitrophenyl)piperazin-1-ium salts

Mahesha¹,

Kumar²,

Yathirajan³

et al. 2022

Acta Cryst E

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“…A bibliography review founded that the piperazine derivatives are employed in many bioactive structures used in various therapeutic areas [2][3][4], e.g., as antifungal [5], antibacterial, antimalarial, and antipsychotic agents [6]. In particular, N-Ethyl piperazine combined with other groups can be used in the synthesis of enrofloxacin, which is an antibiotic used to treat bacterial infections, as well as other pharmaceutical compounds [7]. 1-Ethylpiperazine-1,4-diium bis (hydrogenoxalate) (1EPBH) can be used in drugs for treating epilepsy and cancer diseases.…”

Section: Introductionmentioning

confidence: 99%

DFT and molecular docking study of the effect of a green solvent (water and DMSO) on the structure, MEP, and FMOs of the 1-ethylpiperazine-1,4-diium bis(hydrogenoxalate) compound

Medimagh

Mleh

Issaoui

et al. 2023

Journal of Molecular Liquids

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Towards expansion of the MATTS data bank with heavier elements: the influence of the wavefunction basis set on the multipole model derived from the wavefunction

Ignat'ev,

Dominiak

2024

J Appl Crystallogr

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The MATTS (multipolar atom types from theory and statistical clustering) data bank is an advanced tool for crystal structure refinement and properties analysis. It applies a multipole model (MM), which describes the asphericity of the atomic electron density and helps to interpret X-ray or electron diffraction data better than approaches based on the spherical atoms approximation. The generation of MATTS data involves density functional theory calculations, and until recently we used the B3LYP/6-31G** level of theory for this stage. However, it was not so clear how the wavefunction level of theory, especially the basis set used, influenced the resulting MM. This study investigates the influence of the wavefunction basis set on the resulting MM from a charge density point of view. For this purpose, we used charge density related properties, such as correlation of electrostatic potentials, atomic electron populations and average electrostatic potential values. The complex analysis reveals that, within the framework of MATTS data generation, the size of the basis set used has the most significant impact on the MM's charge density quality, and switching from double- to triple-zeta basis sets helps notably improve the charge density related properties. This research sets the foundation for the creation of a new version of the MATTS data bank, which will be expanded to include atom types for elements heavier than Kr and selected metal complexes important for biological systems.

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Crystal structure studies of 4-ethylpiperazin-1-ium 3,5-dinitrobenzoate, 4-methylpiperazin-1-ium 3,5-dinitrobenzoate and 4-methylpiperazin-1-ium 4-iodobenzoate

Cited by 4 publications

References 34 publications

Crystal structures of six 4-(4-nitrophenyl)piperazin-1-ium salts

Crystal structures of six 4-(4-nitrophenyl)piperazin-1-ium salts

DFT and molecular docking study of the effect of a green solvent (water and DMSO) on the structure, MEP, and FMOs of the 1-ethylpiperazine-1,4-diium bis(hydrogenoxalate) compound

Towards expansion of the MATTS data bank with heavier elements: the influence of the wavefunction basis set on the multipole model derived from the wavefunction

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