MODERN QUANTUM-CHEMICAL STUDY OF THE ELECTRONIC STRUCTURE AND REACTIVITY OF THIOPHENE
Authors
Rustamov Sardor Rustam og’li, Mamarakhmonov Mukhamatdin Khomidovich, Kodirov Abdulakhad Abduraimovich, Khamrayeva K.B., Tokhirova Maryam
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Thiophene is a unique sulfur-containing heterocyclic compound with one sulfur atom. It is a colorless liquid with the formula C4H4S, boiling point 84.1°C, and a benzene-like odor. It is poorly soluble in water but readily soluble in organic solvents. Thiophene continues to fascinate organic chemists with its wide range of chemical properties, ultimately inspiring both theoreticians and experimentalists to conduct fundamental scientific research and conduct new reactions to create innovative organic compounds with high yields. Numerous biologically active drugs are obtained from it, and they are widely used, particularly in agriculture, medicine, and pharmaceuticals. In halogenation, nitration, and formylation reactions, α-substituted products are obtained more rapidly and are exclusively the main products relative to others. Therefore, it is of theoretical interest to identify the key factors behind thiophene's unique behavior by studying its geometric parameters and electronic structure. This article presents the results of quantum chemical calculations performed by us using the Gaussian program to calculate the geometry and electronic structure, and to evaluate the reactivity of thiophene with respect to electrophilic reagents.
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Authors
Rustamov Sardor Rustam og’li, Mamarakhmonov Mukhamatdin Khomidovich, Kodirov Abdulakhad Abduraimovich, Khamrayeva K.B., Tokhirova Maryam
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References:
Alan C. Spivey. Heteroaromatic Chemistry lectures: Pyrroles, furans & thiophenes – properties, syntheses & reactivity. / Imperial College, London. - 2012. 22 pp.
P. Molina, A. Arques, I. Cartagena. Thiophenes and their Benzo Derivatives: Structure. Comprehensive Heterocyclic Chemistry III. Volume 3, 2008, Pages 625-739.
M.A. Yurovskaya, A.V. Kurkin, N.V. Lukashev. Chemistry of aromatic heterocyclic compounds. / Moscow: Faculty of Chemistry of Moscow State University. - 2007. - 50 p.
M. J. Frisch, G. W. Trucks, et al. Gaussian 98, Revision A. 5, Gaussian Inc., Pittsburgh (PA), 1998.
Fahimeh Abedinifar, Elham Babazadeh Rezaei. et all., Recent strategies in the synthesis of thiophene derivatives: highlights from the 2012–2020 literature./ Molecular Diversity (2021) 25:2571–2604 https://doi.org/10.1007/s11030-020-10128-9.
Amita Vyasa, Dharmesh Katariya, et.all., Comprehensive Review on Advances in Thiophene Derivative Synthesis and Their Biological Applications./ Reviews and Advances in Chemistry, 2025, Vol. 15, No. 1, pp. 1–6.
Michael Dewar, Ralph C. Dougherty. The PMO Theory of Organic Chemistry. Springer US, 1975. 576 p.
Dipak Kumar Mandal. Molecular Orbital Theory and Frontier Orbitals for Organic Chemistry./ Elsevier. October 21 2025. https://doi.org/10.1016/C2025-0-00298-3.
M. Kh. Mamarakhmonov, L. I. Belen´kii. et. all. Quantum chemical studies of pyrimidin-4ones Part 6. On peculiarities of the reactions with nitrating agents of some carboxylic acids of the thieno[2,3-d]pyrimidin-4one series and their esters. / Russian Chemical Bulletin, Int. Ed., Vol. 65, No. 3, pp. 654-657, March, 2016.
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