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

Küçük Resim Yok

Tarih

2024

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Elsevier B.V.

Erişim Hakkı

info:eu-repo/semantics/closedAccess

Özet

A 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)

Açıklama

Anahtar Kelimeler

Hirshfeld Surface Analysis, Hydrazone, Pyrazine, Synthesis, Theoretical Calculations, X-ray

Kaynak

Inorganic Chemistry Communications

WoS Q Değeri

Q1

Scopus Q Değeri

Q2

Cilt

169

Sayı

Künye

Mahmoudi, 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.