Differentiation between Isomeric 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles by ESI-HRMS and IR Ion Spectroscopy
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
Differentiation between Isomeric 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles by ESI-HRMS and IR Ion Spectroscopy
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| Автор |
Mazur, D. M.
Piacentino, E. L. Berden, G. Oomens, J. Ryzhov, V. Bakulev, V. A. Lebedev, A. T. |
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| Тематика |
1,2,3-THIADIAZOLES
1,2,3-TRIAZOLES ELECTROSPRAY IONIZATION ISOMER IDENTIFICATION MASS SPECTROMETRY |
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| Описание |
A large variety of 1,2,3-thiadiazoles and 1,2,3-triazoles are used extensively in modern pure and applied organic chemistry as important structural blocks of numerous valuable products. Creation of new methods of synthesis of these isomeric compounds requires the development of reliable analytical tools to reveal the structural characteristics of these novel compounds, which are able to distinguish between isomers. Mass spectrometry (MS) is a clear choice for this task due to its selectivity, sensitivity, informational capacity, and reliability. Here, the application of electrospray ionization (ESI) with ion detection in positive and negative modes was demonstrated to be useful in structural studies. Additionally, interconversion of isomeric 4,5-functionalized 1,2,3-triazoles and 1,2,3-thiadiazoles was demonstrated. Application of accurate mass measurements and tandem mass spectrometry in MS2 and MS3 modes indicated the occurrence of gas-phase rearrangement of 1,2,3-triazoles into 1,2,3-thiadiazoles under (+)ESI-MS/MS conditions, independent of the nature of substituents, in line with the reaction in the condensed phase. Infrared multiple photon dissociation (IRMPD) spectroscopy enabled the establishment of structures of some of the most crucial common fragment ions, including [M+H-N2]+ and [M+H-N2-RSO2]+ species. The (−)ESI-MS/MS experiments were significantly more informative for the sulfonyl alkyl derivatives compared to the sulfonyl aryl ones. However, there was insufficient evidence to confirm the solution-phase transformation of 1,2,3-thiadiazoles into the corresponding 1,2,3-triazoles. © 2023 by the authors.
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| Дата |
2024-04-05T16:15:26Z
2024-04-05T16:15:26Z 2023 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) |info:eu-repo/semantics/publishedVersion |
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| Идентификатор |
Mazur, DM, Piacentino, EL, Berden, G, Oomens, J, Ryzhov, V, Bakulev, VA & Lebedev, AT 2023, 'Differentiation between Isomeric 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles by ESI-HRMS and IR Ion Spectroscopy', Molecules, Том. 28, № 3, 977. https://doi.org/10.3390/molecules28030977
Mazur, D. M., Piacentino, E. L., Berden, G., Oomens, J., Ryzhov, V., Bakulev, V. A., & Lebedev, A. T. (2023). Differentiation between Isomeric 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles by ESI-HRMS and IR Ion Spectroscopy. Molecules, 28(3), [977]. https://doi.org/10.3390/molecules28030977 1420-3049 Final All Open Access, Gold, Green https://www.scopus.com/inward/record.uri?eid=2-s2.0-85147894823&doi=10.3390%2fmolecules28030977&partnerID=40&md5=2d82ae6d854dc66ca8fc897da174f634 https://www.mdpi.com/1420-3049/28/3/977/pdf?version=1674040600 http://elar.urfu.ru/handle/10995/130198 10.3390/molecules28030977 85147894823 000929551500001 |
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| Язык |
en
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| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
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| Формат |
application/pdf
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| Издатель |
MDPI
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| Источник |
Molecules
Molecules |
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