首页 | 本学科首页   官方微博 | 高级检索  
     检索      


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
Authors:Alina Secrieru  Rabah Oumeddour  Maria L S Cristiano
Institution:1.CCMAR and Department of Chemistry and Pharmacy, FCT, Campus de Gambelas, University of Algarve, 8005-039 Faro, Portugal; (A.S.); (R.O.);2.Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK;3.Laboratory of Industrial Analysis and Materials Science, Faculty MISM, University 8 Mai 1945, Guelma 24000, Algeria
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.
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
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号