| Texto completo | |
| Autor(es): |
Dias, Herbert J.
;
Santos, William H.
;
Filho, Luis C. S.
;
Crevelin, Eduardo J.
;
Mcindoe, J. Scott
;
Vessecchi, Ricardo
;
Crotti, Antonio E. M.
Número total de Autores: 7
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Journal of Mass Spectrometry; v. 59, n. 7, p. 14-pg., 2024-07-01. |
| Resumo | |
We have investigated the gas-phase fragmentation reactions of 11 synthetic 4-aryl-3,4-dihydrocoumarins by electrospray ionization tandem mass spectrometry (ESI-MS/MS) on a quadrupole-time-of flight (Q-TOF) hybrid mass spectrometer. We have also estimated thermochemical data for the protonated coumarins (precursor ion A) and product ion structures by computational chemistry at a B3LYP level of theory to establish the ion structures and to rationalize the fragmentation pathways. The most abundant ions in the product ion spectra of coumarins 1-11 resulted from C8H8O2, CO2, C4H4O3, C8H10O3, C8H8O2, and CH3OH eliminations through retro-Diels-Alder (RDA) reactions, remote hydrogen rearrangements (beta-eliminations), and beta-lactone ring contraction. Although the investigated coumarins shared most of the fragmentation pathways, formation of a benzylic product ion and its corresponding tropylium ion was diagnostic of the substituents at ring C. The thermochemical data revealed that the nature and position of the substituents at ring C played a key role in the formation of this product ion and determined its relative intensity in the product ion spectrum. The results of this study contribute to knowledge of the gas-phase ion chemistry of this important class of organic compounds. (AU) | |
| Processo FAPESP: | 16/03036-4 - Investigação do mecanismo de reações multicomponentes catalisadas por metais de transição utilizando espectrometria de massas |
| Beneficiário: | Antônio Eduardo Miller Crotti |
| Modalidade de apoio: | Bolsas no Exterior - Pesquisa |
| Processo FAPESP: | 13/20094-0 - Avaliação da atividade antiparasitária e inseticida de compostos benzofurânicos e estudo de suas reações de fragmentação em fase gasosa empregando espectrometria de massas sequencial |
| Beneficiário: | Antônio Eduardo Miller Crotti |
| Modalidade de apoio: | Auxílio à Pesquisa - Regular |