Email this article 
Quantum Chemical Study of Organic Reactions Mechanisms. XIII. The Reaction of Propargyl Chloride with Potassium 1,2-Ethandithiolate in the System Hydrazine Hydrate–KOH: Heterocyclization Paths
- Authors: Chirkina E.A.1,2, Grabelnykh V.A.1, Korchevin N.A.1,2, Krivdin L.B.1,2, Rosenzweig I.B.1
-
Affiliations:
- A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
- Angarsky State Technical University, ul. Chaikovskogo
- Issue: Vol 60, No 10 (2024)
- Pages: 1054-1069
- Section: Articles
- URL: https://vietnamjournal.ru/0514-7492/article/view/682488
- DOI: https://doi.org/10.31857/S0514749224100083
- EDN: https://elibrary.ru/QLIXDI
- ID: 682488
Cite item
Open Access
Access granted
Subscription or Fee Access
Abstract
Quantum chemical modeling of the mechanism of interaction of propargyl chloride with potassium 1,2-ethanedithiolate in the hydrazine hydrate–KOH system was carried out using the combined approach CCSD(T)/6-31+G*//B3LYP/6-311++G**. The elementary stages of the reaction and possible routes for the heterocyclization of the initial intermediates have been found. Under experimental conditions at a reaction temperature of 40-42°C, 6 hours, 2-methyl-5,6-dihydro-1,4-dithiine was obtained with a yield of 25% and 4,7-dithiadecadiine-2,8 with a yield of 24%. At a temperature of –10 ÷ –15°С, cyclic products are not formed.
About the authors
E. A. Chirkina
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Author for correspondence.
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0002-1733-0685
Russian Federation, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
V. A. Grabelnykh
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0003-1067-7755
ul. Favorskogo, 1, Irkutsk, 664033
N. A. Korchevin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Email: chirkina_ea@mail.ru
Scopus Author ID: 0000-0001-5729-9080
Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
L. B. Krivdin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0003-2941-1084
Russian Federation, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835
I. B. Rosenzweig
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Email: chirkina_ea@mail.ru
ORCID iD: 0000-0001-7817-7816
Russian Federation, , ul. Favorskogo, 1, Irkutsk, 664033
References
- Chirkina E.A., Grabelnykh B.A., Korchevin H.A., Krivdin L.B., Ushakov I.A., Rozentsveig I.B. Structural Chemistry, 2023, 34, 2263–2272. doi: 10.1007/s11224-023-02199-9
- Levanova E.P., Grabelnykh V.A., Vahrina V.S., Albanov A.I., Klyba L.V., Russavskaya N.V., Korchevin N.A., Rozentsveig I.B. J. Sulfur Chem. 2014, 35, 179–187. doi: 10.1080/17415993.2013.849704
- Becke A.D. J. Chem. Phys. 1993, 98, 5648-5652. doi: 10.1063/1.464913
- Lee C., Yang W., Parr R.G. Phys. Rev. B 1988, 37, 785-789. doi: 10.1103/PhysRevB.37.785
- Леванова Е.П., Никонова В.С., Грабельных В.А., Руссавская Н.В., Албанов А.И., Розенцвейг И.Б., Корчевин Н.А. ЖОрХ. 2016, 52, 540–541. [Levanova E.P., Nikonova V.S., Grabelnykh V.A., Russavskaya N.V., Albanov A.I., Rozentsveig I.B., Korchevin N.A. Russ. J. Org. Chem. 2016, 52, 615–623. doi: 10.1134/S1070428016050018
- Gaussian 09, Revision C.01, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G. A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas Ö., Foresman J.B., Ortiz J.V., Cioslowski J., and Fox D.J., Gaussian, Inc., Wallingford CT, 2009.
- Хусайнов З.К., Ойматова Х.Х., Сафаров М.М., Тургунбоев М.Т. Вестник Таджикского нац. универ. Сер. естеств. наук. 2019, 2, 196–203.
- Современные методы органического синтеза. Ред. Т.В. Мандельштам, Б.В. Иоффе, Ю.П. Арцыбашева. Ленинград, 1980.
- Berne B.J., Tuckerman M., Martyna G. J. Chem. Phys. 1991, 94, 6811. doi: 10.1063/1.460259
- González C., Schlegel H.B. J. Phys. Chem. 1990, 94, 5523–5527. doi: 10.1021/j100377a021
- González C., Schlegel H.B. J. Chem. Phys. 1991, 95, 5853. doi: 10.1063/1.461606
Supplementary files
