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Mass Spectra of New Heterocycles: XXVI. Electron Impact Ionization Study of N-(5-Amino­thiophen-2-yl)- and N-[2-(Methylsulfanyl)-1,3-thiazol-5-yl]­isothioureas

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Abstract

The behavior of a series of previously unknown N-(5-aminothiophen-2-yl)- and N-[2-(methyl­sulfanyl)-1,3-thiazol-5-yl]isothioureas under electron impact ionization (70 eV) has been studied for the first time. 2-Thienylisothioureas give rise to a fairly stable molecular ion (Irel 11–25%), whereas no molecular ion peak is present in the mass spectra of 1,3-thiazolylisothioureas. A common fragmentation pathway of the molecular ions of 2-thienyl- and 1,3-thiazolylisothioureas involves cleavage of the C–N bond in the isothiourea fragment with charge localization on the imino nitrogen atom to give [R3SC≡NR2]+ ion (Irel 34–100%); furthermore, [M – R3SC=NR2]+ ion with charge localization on the amino nitrogen atom is formed from thienyl derivatives and is the most abundant (Irel 91–100%). The mass spectra of 1,3-thiazolylisothioureas also showed [M – MeSCN]+· and [MeSCS]+ ion peaks resulting from decomposition of the thiazole ring in the molecular ion. In addition, unlike 2-thienylisothioureas, the molecular ions of 1,3-thiazolyl analogs underwent Chet–N bond cleavage with charge localization on the thiazole fragment.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the Baikal joint analytical center, Siberian Branch, Russian Academy of Sciences.

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  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    L. V. Klyba, E. R. Sanzheeva, N. A. Nedolya & O. A. Tarasova

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  1. L. V. Klyba
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  2. E. R. Sanzheeva
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  3. N. A. Nedolya
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Correspondence to L. V. Klyba.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 7, pp. 895–903 https://doi.org/10.31857/S0514749223070030.

For communication XXV, see [1].

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Klyba, L.V., Sanzheeva, E.R., Nedolya, N.A. et al. Mass Spectra of New Heterocycles: XXVI. Electron Impact Ionization Study of N-(5-Amino­thiophen-2-yl)- and N-[2-(Methylsulfanyl)-1,3-thiazol-5-yl]­isothioureas. Russ J Org Chem 59, 1136–1143 (2023). https://doi.org/10.1134/S1070428023070035

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