Synthesis, structural characterization, antibacterial activity, DFT computational studies and thermal analysis of two new thiocyanate compounds based on 1-phenylpiperazine

Gharbi, Chaima; Toumi, Baya; Soudani, Sarra; Lefèbvre, Frédéric; Kaminsky, Werner; Jelsch, Christian; Nasr, C. Ben; Khedhiri, Lamia

doi:10.1016/j.molstruc.2022.132620

Cited by 12 publications

(2 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Piperazines and their derivatives have attracted growing attention for years (Berkheij et al, 2005;Elliott, 2011;Asif, 2015;Brito et al, 2019), mainly because of their multivalent biological profiles in a number of different therapeutic areas (Upadhayaya et al, 2004;Chaudhary et al, 2006;Kharb et al, 2012). The pharmacological significance of piperazines is also manifested in the application of its framework in the assemblies of inclusion, hybrid and other functional materials (Brockunier et al, 2004;Bogatcheva et al, 2006;Jin et al, 2020;Gharbi et al, 2022). Among them, a potential application for 4-nitrophenylpiperazine (NPP) can be indicated (Ko ¨nig et al, 1997;Lu, 2007;Wang et al, 2014).…”

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4][5][6]. The pharmacological significance of piperazine derivatives has made them very important ligands for the synthesis of inclusion compounds [7][8][9] and hybrid materials [10][11][12]. Furthermore, the phenylpiperazine framework is one of special pharmaceutical interest because it has been known as active against many subtypes of serotonin receptors [13,14].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-Bonded Chain of Rings Motif in N-(4-Methoxyphenyl)piperazin-1-ium Salts with Benzoate Anions: Supramolecular Assemblies and Their Energy Frameworks

Priyanka¹,

Jayanna²,

Divakara³

et al. 2022

Crystals

View full text Add to dashboard Cite

The crystal structures of three salts, namely N-(4-methoxyphenyl)piperazin-1-ium ethoxybenzoate monohydrate (I), N-(4-methoxyphenyl)piperazin-1-ium methoxybenzoate monohydrate (II) and N-(4-methoxyphenyl)piperazin-1-ium hydroxybenzoate monohydrate (III), have been determined and compared. In each of them, the ionic components and the water molecules are linked by a combination of N—H···O and O—H···O hydrogen bonds to form infinite chains of edge-fused centrosymmetric rings running parallel to the [100] direction. The C—H···O, C—H···π(arene) interactions and O—H···O in (III) are responsible for the further propagation of the aforementioned chains into di-periodic layers or tri-periodic networks. From an energetic point of view, all structures are primarily di-periodic; the very strong ionic interactions determine the periodicity. For comparison purposes, quantum chemical calculations were performed to show the difference between the ionic and neutral components. The energy of the hydrogen-bonded ring motifs was also estimated.

show abstract

KSCN‐Mediated One‐Pot Thiocyanation Tandem Cyclization of Enaminones: a Facile Access to 2‐amino/imino Thiazolo Fused Chromone and Coumarin Frameworks

Kumawat,

Mansuri,

Sravani Galla

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

A rapid metal‐free approach describing one‐pot thiocyanation of chromone and coumarin enabling tandem cyclization via potassium thiocyanate as a sulfur surrogate was unveiled. Interestingly, this enaminone‐mediated protocol facilitated straightforward access to medicinally significant 2‐amino/imino thiazolo fused chromone and coumarin frameworks. This methodology provided good atom‐economy, remarkable functional group tolerance, and scalability. Alongside establishing a wide substrate scope, it also provided a feasible scalability up to gram scale.

show abstract

Synthesis, structural characterization, antibacterial activity, DFT computational studies and thermal analysis of two new thiocyanate compounds based on 1-phenylpiperazine

Cited by 12 publications

References 69 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

Hydrogen-Bonded Chain of Rings Motif in N-(4-Methoxyphenyl)piperazin-1-ium Salts with Benzoate Anions: Supramolecular Assemblies and Their Energy Frameworks

KSCN‐Mediated One‐Pot Thiocyanation Tandem Cyclization of Enaminones: a Facile Access to 2‐amino/imino Thiazolo Fused Chromone and Coumarin Frameworks

Contact Info

Product

Resources

About