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The Influence of Hydrazo and Azo Bonds on the Conformation of New 4-Methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and Its Azo Derivative—Structural Properties, Vibrational Spectra and Quantum Chemical DFT Calculations
Autorzy
Rok wydania
2025
Czasopismo
International Journal of Molecular Sciences
Numer woluminu
26
Strony
12106/1-12106/24
DOI
10.3390/ijms262412106
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A review of studies has shown that aromatic azo and hydrazo derivatives are used in a wide spectrum of fields, including food, pharmaceutical, and cosmetic products, as well as in technical and electronic technologies, which has contributed to the development of new such compounds. In this work, the structures of newly obtained 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine (4MDNPHP) and its azo derivative, 4-methyl-3,5-dinitro-2-[(E)-phenyldiazenyl]pyridine (4MDNPAP), were established by spectroscopic (NMR, IR, Raman, and UV-Vis) and emission studies. Single-crystal X-ray diffraction analysis was used to determine the molecular structure of the studied compounds, and the results were compared with DFT calculations (B3LYP/6-311G(2d,2p)). The collected X-ray data revealed that the crystal of the hydrazo compound (4MDNPHP) belongs to the triclinic space group P1̲ (Z = 2), whereas the crystal of the azo compound (4MDNPAP) follows the symmetry of the monoclinic space group P21/n (Z = 4). Both presented derivatives crystallized with one molecule in the asymmetric unit. Specific properties of the hydrazo bridge Cϕ-NH-NH-Cθ moiety and its azo counterpart Cϕ-N=N-Cθ were considered in detail.
Słowa kluczowe
azo and hydrazo groups, pyridine derivatives, crystal structures, spectroscopic analyses, DFT calculations
Licencja otwartego dostępu
Licencja na prawach której można swobodnie kopiować, rozprowadzać, zmieniać i remiksować objęty prawem autorskim utwór (Utwór-przedmiot prawa autorskiego) pod warunkiem podania imienia i nazwiska autora utworu pierwotnego oraz źródła pochodzenia utworu.
Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.3390/ijms262412106
Strona internetowa wydawcy
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