Utilize este identificador para referenciar este registo:
https://hdl.handle.net/10316/101239
Campo DC | Valor | Idioma |
---|---|---|
dc.contributor.author | Reva, Igor | - |
dc.contributor.author | Jesus, A. J. Lopes | - |
dc.contributor.author | Nunes, Cláudio M | - |
dc.contributor.author | Roque, José P. L. | - |
dc.contributor.author | Fausto, Rui | - |
dc.date.accessioned | 2022-08-17T16:40:49Z | - |
dc.date.available | 2022-08-17T16:40:49Z | - |
dc.date.issued | 2021 | - |
dc.identifier.issn | 0022-3263 | pt |
dc.identifier.issn | 1520-6904 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/101239 | - |
dc.description.abstract | The monomers of 1,3-benzoxazole isolated in a cryogenic argon matrix were characterized by infrared spectroscopy. The photochemistry of matrix-isolated 1,3-benzoxazole, induced by excitation with a frequency-tunable narrowband UV light, was investigated. Irradiation at 233 nm resulted in a nearly quantitative conversion of 1,3-benzoxazole into 2-isocyanophenol. The individual photochemical behavior of the in situ produced 2-isocyanophenol was studied upon excitations at 290 nm, where 1,3-benzoxazole does not react. The photochemistry of isomeric matrix-isolated 2-cyanophenol was also studied. The photoreactions of 2-substituted (cyano- or isocyano-) phenols were found to have many similarities: (i) OH bond cleavage, yielding a 2-substituted (cyano- or isocyano-) phenoxyl radical and an H-atom, (ii) recombination of the detached H-atom, resulting in an oxo tautomer, and (iii) decomposition leading to fulvenone, together with HCN and HNC. In another photoprocess, 2-cyanophenol undergoes a [1,5] H-shift from the hydroxyl group to the cyano group yielding isomeric ketenimine. The analogous [1,5] H-shift from the hydroxyl group to the isocyano group must have also occurred in 2-isocyanophenol; however, the resulting nitrile ylide isomer is kinetically unstable and collapses to benzoxazole. All photoproducts were characterized by comparing their observed infrared spectra with those computed at the B3LYP/6-311++G(d,p) level. The mechanistic analysis of the photochemistry occurring in the family of the title compounds is presented. | pt |
dc.language.iso | eng | pt |
dc.publisher | American Chemical Society | pt |
dc.relation | info:eu-repo/grantAgreement/POCI-01-0145-FEDER-028973/PT | pt |
dc.relation | UIDB/00313/2020 | pt |
dc.relation | UIDB/00102/2020 | pt |
dc.relation | UIDP/00313/2020 | pt |
dc.relation | UIDP/00102/2020 | pt |
dc.rights | embargoedAccess | pt |
dc.title | UV-Induced Photochemistry of 1,3-Benzoxazole, 2-Isocyanophenol, and 2-Cyanophenol Isolated in Low-Temperature Ar Matrixes | pt |
dc.type | article | - |
degois.publication.firstPage | 6126 | pt |
degois.publication.lastPage | 6137 | pt |
degois.publication.issue | 9 | pt |
degois.publication.title | The Journal of Organic Chemistry | pt |
dc.relation.publisherversion | https://doi.org/10.1021/acs.joc.0c02970 | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.1021/acs.joc.0c02970 | pt |
degois.publication.volume | 86 | pt |
dc.date.embargo | 2022-01-01 | * |
uc.date.periodoEmbargo | 365 | pt |
item.fulltext | Com Texto completo | - |
item.grantfulltext | open | - |
item.languageiso639-1 | en | - |
item.cerifentitytype | Publications | - |
item.openairetype | article | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
crisitem.project.grantno | Coimbra Chemistry Center | - |
crisitem.project.grantno | CIEPQPF- Chemical Engineering and Renewable Resources for Sustainability | - |
crisitem.project.grantno | Coimbra Chemistry Center | - |
crisitem.project.grantno | CERES - Chemical Engineering and Renewable Resources for Sustainability | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0001-5983-7743 | - |
crisitem.author.orcid | 0000-0002-5953-976X | - |
crisitem.author.orcid | 0000-0002-8511-1230 | - |
crisitem.author.orcid | 0000-0002-7845-9415 | - |
crisitem.author.orcid | 0000-0002-8264-6854 | - |
Aparece nas coleções: | I&D CQC - Artigos em Revistas Internacionais |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
---|---|---|---|---|
JOC-2021-86-6126.pdf | 1.55 MB | Adobe PDF | Ver/Abrir |
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