Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study

被引：0

作者：

Lapczuk, Agnieszka ^{[1
]}

Rios-Gutierrez, Mar ^{[2
]}

机构：

[1] Cracow Univ Technol, Dept Organ Chem & Technol, Warszawska 24, PL-31155 Krakow, Poland

[2] Univ Valencia, Dept Organ Chem, Dr Moliner 50, Burjassot 46100, Valencia, Spain

来源：

MOLECULES | 2025年 / 30卷 / 01期

关键词：

3+2] cycloaddition; nitrilimine; reactivity; molecular mechanism; molecular electron density theory; 1,2,4-triazole; TOPOLOGICAL ANALYSIS; LOCALIZATION; FLUORINE; DFT;

D O I：

10.3390/molecules30010085

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In this study, we investigated the [3+2] cycloaddition reaction of CF3CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared the resulting isomers. We determined the preferred reaction pathway by examining the electrophilic and nucleophilic properties of the reaction substrates, performing thermodynamic calculations for the individual pathways, and comparing them with the experimental results.

引用

页数：18

共 77 条

[1] Recent advances in the chemistry of 1,2,4-triazoles: Synthesis, reactivity and biological activities
Abdelli, Abderrahmen
Azzouni, Safa
Plais, Romain
Gaucher, Anne
Efrit, Mohamed Lotfi
Prim, Damien
[J]. TETRAHEDRON LETTERS, 2021, 86
[2] A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes
Aurell, MJ
Domingo, LR
Pérez, P
Contreras, R
[J]. TETRAHEDRON, 2004, 60 (50) : 11503 - 11509
[3] A SIMPLE MEASURE OF ELECTRON LOCALIZATION IN ATOMIC AND MOLECULAR-SYSTEMS
BECKE, AD
EDGECOMBE, KE
[J]. JOURNAL OF CHEMICAL PHYSICS, 1990, 92 (09) : 5397 - 5403
[4] Novel functionalized β-nitrostyrenes: Promising candidates for new antibacterial drugs
Boguszewska-Czubara, Anna
Kula, Karolina
Wnorowski, Artur
Biernasiuk, Anna
Popiolek, Lukasz
Miodowski, Dawid
Demchuk, Oleg M.
Jasinski, Radomir
[J]. SAUDI PHARMACEUTICAL JOURNAL, 2019, 27 (04) : 593 - 601
[5] Borysov O.V., 2023, Chem. Heterocycl. Compd, V59, P429, DOI [10.1007/s10593-023-03213-y, DOI 10.1007/S10593-023-03213-Y]
[6] Triazole derivatives inhibit the VOR complex-mediated nuclear transport of extracellular particles: Potential application in cancer and HIV-1 infection
Carbone, Daniela
Santos, Mark F.
Corbeil, Denis
Vistoli, Giulio
Parrino, Barbara
Karbanova, Jana
Cascioferro, Stella
Pecoraro, Camilla
Bauson, Jodi
Eliwat, Waleed
Aalam, Feryal
Cirrincione, Girolamo
Lorico, Aurelio
Diana, Patrizia
[J]. BIOORGANIC CHEMISTRY, 2024, 150
[7] Synthesis, Spectroscopic and Thermal Characterization of Azido-1,2,4-triazoles: A Class of Heteroarenes with a High Nitrogen Content
Cardillo, Paolo
Dellavedova, Marco
Gigante, Lucia
Lunghi, Angelo
Pasturenzi, Christian
Salatelli, Elisabetta
Zanirato, Paolo
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (06) : 1195 - 1201
[8] Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections
Chai, Jeng-Da
Head-Gordon, Martin
[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2008, 10 (44) : 6615 - 6620
[9] Synthesis methods of 1,2,3-/1,2,4-triazoles: A review
Dai, Jinlian
Tian, Sen
Yang, Xueqing
Liu, Zongliang
[J]. FRONTIERS IN CHEMISTRY, 2022, 10
[10] Fused Triazole-Azepine Hybrids as Potential Non-Steroidal Antiinflammatory Agents
Demchenko, Sergii
Lesyk, Roman
Yadlovskyi, Oleh
Holota, Serhii
Yarmoluk, Sergii
Tsyhankov, Sergii
Demchenko, Anatolii
[J]. SCIENTIA PHARMACEUTICA, 2023, 91 (02)

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