Secrieru, Alina, Oumeddour, Rabah and Cristiano, Maria LS
(2021)
Substituent Effects on EI-MS Fragmentation Patterns of 5-Allyloxy-1-aryl-tetrazoles and 4-Allyl-1-aryl-tetrazole-5-ones; Correlation with UV-Induced Fragmentation Channels.
MOLECULES, 26 (11).
3282-.
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Substituent Effects on EI-MS Fragmentation Patterns of 5-Allyloxy-1-aryl-tetrazoles and 4-Allyl-1-aryl-tetrazole-5-ones; Cor.pdf - Published version Download (3MB) | Preview |
Abstract
1,4- and 1,5-disubstituted tetrazoles possess enriched structures and versatile chemistry, representing a challenge for chemists. In the present work, we unravel the fragmentation patterns of a chemically diverse range of 5-allyloxy-1-aryl-tetrazoles and 4-allyl-1-aryl-tetrazolole-5-ones when subjected to electron impact mass spectrometry (EI-MS) and investigate the correlation with the UV-induced fragmentation channels of the matrix-isolated tetrazole derivatives. Our results indicate that the fragmentation pathways of the selected tetrazoles in EI-MS are highly influenced by the electronic effects induced by substitution. Multiple pathways can be envisaged to explain the mechanisms of fragmentation, frequently awarding common final species, namely arylisocyanate, arylazide, arylnitrene, isocyanic acid and hydrogen azide radical cations, as well as allyl/aryl cations. The identified fragments are consistent with those found in previous investigations concerning the photochemical stability of the same class of molecules. This parallelism showcases a similarity in the behaviour of tetrazoles under EI-MS and UV-irradiation in the inert environment of cryogenic matrices of noble gases, providing efficient tools for reactivity predictions, whether for analytical ends or more in-depth studies. Theoretical calculations provide complementary information to articulate predictions of resulting products.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | 5-allyloxy-1-aryl-tetrazoles, 4-allyl-1-aryl-tetrazole-5-ones, mass spectrometry, electron impact, fragmentation patterns, matrix isolation, UV-induced fragmentation, substituent effects |
| Divisions: | Faculty of Science and Engineering > School of Physical Sciences |
| Depositing User: | Symplectic Admin |
| Date Deposited: | 09 Dec 2021 16:51 |
| Last Modified: | 18 Jan 2023 21:23 |
| DOI: | 10.3390/molecules26113282 |
| Open Access URL: | https://www.mdpi.com/1420-3049/26/11/3282 |
| Related URLs: | |
| URI: | https://livrepository.liverpool.ac.uk/id/eprint/3145097 |
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