Synthesis, crystal structure, exploration of the supramolecular assembly through Hirshfeld surface analysis of new 2,4-dihydro-1H-1,2,4-triazole-3-selones and 3,3′-di(4H-1,2,4-triazolyl)diselenides

Synthesis, crystal structure, exploration of the supramolecular assembly through Hirshfeld surface analysis of new 2,4-dihydro-1H-1,2,4-triazole-3-selones and 3,3′-di(4H-1,2,4-triazolyl)diselenides Full article

Journal

Journal of Organometallic Chemistry
ISSN: 1872-8561 , E-ISSN: 0022-328X

Output data

Year: 2024, Volume: 1006, Article number : 123019, Pages count : DOI: 10.1016/j.jorganchem.2024.123019

Authors

Askerov Rizvan Kamil oglu ¹ , El Bakri Youness ² , Osmanov Vladimir Kimovich ³ , Ahsin Atazaz ^4,5 , Chipinsky Evgeny Vadimovich ³ , Vladimirovna Matsulevich Zhanna ³ , Lukiyanova Julia Mikhailovna ³ , Kovaleva Olga Nikolaevna ³ , Khrustalev Victor Nikolaevich ^6,7 , Sergeevich Peregudov Alexander ⁸ , Baranov Evgeny Vladimirovich ⁹ , Magerramov Abel Mammadali oglu ¹ , Al-Salahi Rashad ¹⁰ , Borisov Aleksandr Vladimirovich ³

Affiliations

1	Baku State University, Baku, Azerbaijan
2	Department of Theoretical and Applied Chemistry, South Ural State University, Lenin prospect 76, Chelyabinsk, 454080, Russia
3	R.A. Alekseev State Technical University, Nizhny Novgorod, 603950, Russia
4	Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
5	School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
6	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia
7	Peoples’ Friendship University of Russia (RUDN), Moscow, 117198, Russia
8	A.N. Nesmeyanov Institute of Organoelement compounds, Russian Academy of Sciences, Moscow, Russia
9	G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhny Novgorod, 603950, Russia
10	Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

The reaction of aromatic ring-substituted isoselenocyanates with 2-thiopheacetic and 4-pyridinecarboxylic acid hydrazides yielded selenosemicarbazides, which were further converted into previously unknown 1,2,4-triazole-3-selones and 3,3′-di(4H-1, 2,4-triazolyl)diselenides. The structure of the obtained compounds was studied by X-ray diffraction analysis and NMR spectroscopy. Theoretically, the reactivity and nonlinear optical (NLO) properties were predicted by using the DFT-B3LYP method. Charge separation and orbital analysis were performed by using the frontier molecular orbital (FMO) and natural population analysis (NPA). 5aa, 5ca, and 5ab show significantly reduced HOMO-LUMO gaps and ionization potential (IP) among the other compounds. The density of states (DOS) spectra was plotted to get a pictorial representation of orbital and their energies. The highest βo value of 1754.31 au is obtained for 7fb which is indicating its excellent NLO properties. Nature and strength of Intermolecular interactions in crystal packing is considered through Hirshfeld surface (HS) analysis using the CrystalExplorer. Hence, the studied compounds have significant reactivity and NLO properties and may open a new door in searching for new NLO materials.

Askerov R.K.o. , El Bakri Y. , Osmanov V.K. , Ahsin A. , Chipinsky E.V. , Vladimirovna M.Z. , Lukiyanova J.M. , Kovaleva O.N. , Khrustalev V.N. , Sergeevich P.A. , Baranov E.V. , Magerramov A.M.o. , Al-Salahi R. , Borisov A.V.
Synthesis, crystal structure, exploration of the supramolecular assembly through Hirshfeld surface analysis of new 2,4-dihydro-1H-1,2,4-triazole-3-selones and 3,3′-di(4H-1,2,4-triazolyl)diselenides
Journal of Organometallic Chemistry. 2024. V.1006. 123019 . DOI: 10.1016/j.jorganchem.2024.123019 WOS Scopus OpenAlex

Web of science:	WOS:001164621300001
Scopus:	2-s2.0-85182021264
OpenAlex:	W4390653027

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