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http://hdl.handle.net/1843/55429| Type: | Artigo de Periódico |
| Title: | On-surface multicomponent Povarov reaction examined by paper spray mass spectrometry |
| Authors: | João Victor Coelho Pimenta Adão Aparecido Sabino Rodinei Augusti |
| Abstract: | Povarov multicomponent reaction (MCR) is an acid-catalyzed process that uses three distinct classes of reactants. i. e. an aldehyde, aniline, and activated alkene. We employ paper spray ionization mass spectrometry (PS-MS) as a convenient platform for investigating the on-surface Povarov reaction using the following suitable prototype starting reactants: the tag-charged aldehyde 1, 4-bromoaniline, 2,3-dihydrofuran, and formic acid. The PS(þ)-MS revealed, besides the formation of the Povarov product (a tetrahydroquinoline compound), the transitional imine. Moreover, the oxonium intermediate was also detected as the water and formic acid adducts. Other alkenes (2,3-dihydropyran and styrene), acid catalysts (acetic acid and p-sulfonic acid calix[4]arene), and aldehydes (4-nitrobenzaldehyde, 4-anisaldehyde, 4-methoxycinnamaldehyde, citronellal, and valeraldehyde) were employed to verify the reaction generality. We observed that styrene (an unactivated alkene), p-sulfonic acid calix [4] arene (an acid with a non-nucleophilic conjugated base), and aromatic aldehydes (4-nitrobenzaldehyde and 4-anisaldehyde) showed lower reactivity than the other reactants. In conclusion, an exciting possibility emerges as PS-MS can be widely employed to investigate similar on-surface organic reactions to verify the connections between the on-surface and condensed phase processes. |
| Subject: | Espectrometria de massa Quimica de superficie Ressonancia magnetica nuclear Aldeídos Olefinas Química orgânica Matéria condensada |
| language: | eng |
| metadata.dc.publisher.country: | Brasil |
| Publisher: | Universidade Federal de Minas Gerais |
| Publisher Initials: | UFMG |
| metadata.dc.publisher.department: | ICX - DEPARTAMENTO DE QUÍMICA |
| Rights: | Acesso Restrito |
| metadata.dc.identifier.doi: | https://doi.org/10.1016/j.ijms.2021.116775 |
| URI: | http://hdl.handle.net/1843/55429 |
| Issue Date: | 2021 |
| metadata.dc.url.externa: | https://www.sciencedirect.com/science/article/pii/S1387380621002566 |
| metadata.dc.relation.ispartof: | International Journal of Mass Spectrometry |
| Appears in Collections: | Artigo de Periódico |
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