Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | https://doi.org/10.1039/c7ra00408g |
Resumo: | Proc. 2005/51850-9 and 2014/50316-7. POCI-01-0145-FEDER-007265. |
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oai:run.unl.pt:10362/70509 |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP dataChemistry(all)Chemical Engineering(all)Proc. 2005/51850-9 and 2014/50316-7. POCI-01-0145-FEDER-007265.Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N-CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometric analysis in order to identify structural features influencing fragmentation. Most of the amides showed an intense signal of the protonated molecule [M + H]+ when subjected to both HRESI-MS and EI-MS conditions, with a common outcome being the cleavage of the amide bond (N-CO). This results in the loss of the neutral amine or lactam and the formation of aryl acylium cations. The mechanism of N-CO bond cleavage persists in α,β-unsaturated amides because of the stability caused by extended conjugation. Computational methods determined that the protonation of the piperamides and their derivatives takes place preferentially at the amide nitrogen supporting the dominant the N-CO bond cleavage.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNFokoue, H. H.Marques, Joaquim VogtCorreia, Mauro VicentiniYamaguchi, L. F.Qu, X.Aires-De-Sousa, J.Scotti, M. T.Lopes, N. P.Kato, M. J.2019-05-22T22:13:11Z20182018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article7application/pdfhttps://doi.org/10.1039/c7ra00408geng2046-2069PURE: 5112211http://www.scopus.com/inward/record.url?scp=85048824789&partnerID=8YFLogxKhttps://doi.org/10.1039/c7ra00408ginfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T04:33:23Zoai:run.unl.pt:10362/70509Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:35:06.380388Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
| dc.title.none.fl_str_mv |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| title |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| spellingShingle |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data Fokoue, H. H. Chemistry(all) Chemical Engineering(all) |
| title_short |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| title_full |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| title_fullStr |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| title_full_unstemmed |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| title_sort |
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data |
| author |
Fokoue, H. H. |
| author_facet |
Fokoue, H. H. Marques, Joaquim Vogt Correia, Mauro Vicentini Yamaguchi, L. F. Qu, X. Aires-De-Sousa, J. Scotti, M. T. Lopes, N. P. Kato, M. J. |
| author_role |
author |
| author2 |
Marques, Joaquim Vogt Correia, Mauro Vicentini Yamaguchi, L. F. Qu, X. Aires-De-Sousa, J. Scotti, M. T. Lopes, N. P. Kato, M. J. |
| author2_role |
author author author author author author author author |
| dc.contributor.none.fl_str_mv |
LAQV@REQUIMTE DQ - Departamento de Química RUN |
| dc.contributor.author.fl_str_mv |
Fokoue, H. H. Marques, Joaquim Vogt Correia, Mauro Vicentini Yamaguchi, L. F. Qu, X. Aires-De-Sousa, J. Scotti, M. T. Lopes, N. P. Kato, M. J. |
| dc.subject.por.fl_str_mv |
Chemistry(all) Chemical Engineering(all) |
| topic |
Chemistry(all) Chemical Engineering(all) |
| description |
Proc. 2005/51850-9 and 2014/50316-7. POCI-01-0145-FEDER-007265. |
| publishDate |
2018 |
| dc.date.none.fl_str_mv |
2018 2018-01-01T00:00:00Z 2019-05-22T22:13:11Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
https://doi.org/10.1039/c7ra00408g |
| url |
https://doi.org/10.1039/c7ra00408g |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
2046-2069 PURE: 5112211 http://www.scopus.com/inward/record.url?scp=85048824789&partnerID=8YFLogxK https://doi.org/10.1039/c7ra00408g |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
7 application/pdf |
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reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799137972517339136 |