Novel benzoyl and acetyl pyrazine-2-carbohydrazonamide hybrid derivatives: Experimental and theoretical insights

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dc.authorscopusidGhodrat Mahmoudi / 15765751200
dc.authorwosidGhodrat Mahmoudi / AAB-6892-2022
dc.contributor.authorMahmoudi, Ghodrat
dc.contributor.authorGarcia Santos, Isabel
dc.contributor.authorCastiñeiras, Alfonso
dc.contributor.authorServati Gargari, Masoumeh
dc.contributor.authorFrontera, Antonio
dc.contributor.authorSafin, Damir A.
dc.date.accessioned2025-04-18T10:07:38Z
dc.date.available2025-04-18T10:07:38Z
dc.date.issued2024
dc.departmentİstinye Üniversitesi, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümü
dc.description.abstractA series of novel benzoyl and acetyl pyrazine-2-carbohydrazonamide hybrid derivatives, namely N’-benzoylpyrazine-2-carbohydrazonamide (1), N’-(4-methylbenzoyl)pyrazine-2-carbohydrazonamide (2), N’-(2-phenylacetyl)pyrazine-2-carbohydrazonamide (3) and N’-(2-(1H-indol-3-yl)acetyl)pyrazine-2-carbohydrazonamide (4), were readily obtained using a metallic Na-assisted interaction of 2-cyanopyrazine with benzohydrazide, 4-methylbenzohydrazide, 2-phenylacetohydrazide or 2-(1H-indol-3-yl)acetohydrazide in dry MeOH. Compounds 1–4 were studied by a set of physical measurements, including FTIR, 1H NMR and UV–vis spectroscopy, while their crystal structures were elucidated by single crystal X-ray diffraction and the corresponding crystal packing was further studied in detail using the Hirshfeld surface analysis. Compounds 3 and 4 were found to adopt both the E- and Z-isomeric forms in DMSO‑d6. Molecules of the title compounds are linked via N[sbnd]H⋯O and N[sbnd]H⋯N hydrogen bonds and π⋯π interactions, yielding supramolecular aggregates. As it was found by the Hirshfeld surface analysis, molecules of 1–4 mainly interact through the H⋯X (X = H, C, N and O) and C⋯X (X = C and N) contacts. The molecular interactions were quantified and compared using DFT calculations, molecular electrostatic potential (MEP) analysis and quantum theory of atoms in molecules (QTAIM) analysis, highlighting the dominant role of hydrogen bonding interactions in governing the crystal packing. © 2024 The Author(s)
dc.description.sponsorshipThis work was supported by the grant from the Russian Science Foundation (No. 24-23-00118).
dc.identifier.citationMahmoudi, G., Garcia-Santos, I., Castiñeiras, A., Gargari, M. S., Frontera, A., & Safin, D. A. (2024). Novel benzoyl and acetyl pyrazine-2-carbohydrazonamide hybrid derivatives: Experimental and theoretical insights. Inorganic Chemistry Communications, 169, 112990.
dc.identifier.doi10.1016/j.inoche.2024.112990
dc.identifier.issn13877003
dc.identifier.scopus2-s2.0-85202040178
dc.identifier.scopusqualityQ2
dc.identifier.urihttp://dx.doi.org/10.1016/j.inoche.2024.112990
dc.identifier.urihttps://hdl.handle.net/20.500.12713/6951
dc.identifier.volume169
dc.identifier.wosWOS:001302222100001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakScopus
dc.indekslendigikaynakWeb of Science
dc.institutionauthorMahmoudi, Ghodrat
dc.institutionauthoridGhodrat Mahmoudi / 0000-0002-4846-5283
dc.language.isoen
dc.publisherElsevier B.V.
dc.relation.ispartofInorganic Chemistry Communications
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectHirshfeld Surface Analysis
dc.subjectHydrazone
dc.subjectPyrazine
dc.subjectSynthesis
dc.subjectTheoretical Calculations
dc.subjectX-ray
dc.titleNovel benzoyl and acetyl pyrazine-2-carbohydrazonamide hybrid derivatives: Experimental and theoretical insights
dc.typeArticle

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