A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate

Detalhes bibliográficos
Autor(a) principal: Camuenho, Ambrósio
Data de Publicação: 2019
Outros Autores: Jorge Parola, A., Alejo-Armijo, Alfonso, Pandian, Ramesh, Gomes, Clara S. B., Laia, César A. T., Pina, Fernando
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/91641
Resumo: UID/QUI/50006/2019. PTDC/QEQ-QFI/1971/2014. PTDC/QUI-COL/32351/2017. PTDC/QUI-QFI/30951/2017. grant no. 219201.
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spelling A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistateCatalysisChemistry(all)Materials ChemistryUID/QUI/50006/2019. PTDC/QEQ-QFI/1971/2014. PTDC/QUI-COL/32351/2017. PTDC/QUI-QFI/30951/2017. grant no. 219201.Anthocyanins and related flavylium derivatives exist in aqueous solution as a pH-dependent mole fraction distribution of species (a multistate system) with known biological activity. Introduction of nitrogen heterocycles in the flavylium core can lead to multistates with different constitution and increased activity. Compound 1, a diethylamino derivative of 4-pyridinechalcone, was synthesized and characterized by X-ray crystallography, showing a pH-dependent reaction network similar to anthocyanins and related compounds. The several species present at the equilibrium multistate were fully characterized by 1H NMR and 13C NMR. The thermodynamics and kinetics of the multistate were studied through pH jumps followed by 1H NMR and UV-vis absorption including stopped-flow for the faster kinetic steps. In the parent 4-pyridinechalcone compound, protonation of the pyridine nitrogen for pH 4 prevents formation of the flavylium cation. In compound 1, the first protonation takes place in the diethylamino substituent and in acidic medium, two new flavylium derivatives, a single (2 pH 4) and a double (pH 1) positively charged species, in equilibrium with protonated hemiketal, cis and trans chalcones, have been characterized. Differently from anthocyanins and related compounds, experimental evidence for an unexpected very slow (0.0003 s-1) ring opening-closure between the hemiketal and the cis-chalcone (tautomerization) was achieved.LAQV@REQUIMTEDQ - Departamento de QuímicaUCIBIO - Applied Molecular Biosciences UnitRUNCamuenho, AmbrósioJorge Parola, A.Alejo-Armijo, AlfonsoPandian, RameshGomes, Clara S. B.Laia, César A. T.Pina, Fernando2022-04-02T00:31:03Z2019-01-012019-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article11application/pdfhttp://hdl.handle.net/10362/91641eng1144-0546PURE: 16445850https://doi.org/10.1039/c9nj04776jinfo: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:RCAAP2024-03-11T04:40:46Zoai:run.unl.pt:10362/91641Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:37:23.619193Repositório 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 A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
title A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
spellingShingle A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
Camuenho, Ambrósio
Catalysis
Chemistry(all)
Materials Chemistry
title_short A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
title_full A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
title_fullStr A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
title_full_unstemmed A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
title_sort A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate
author Camuenho, Ambrósio
author_facet Camuenho, Ambrósio
Jorge Parola, A.
Alejo-Armijo, Alfonso
Pandian, Ramesh
Gomes, Clara S. B.
Laia, César A. T.
Pina, Fernando
author_role author
author2 Jorge Parola, A.
Alejo-Armijo, Alfonso
Pandian, Ramesh
Gomes, Clara S. B.
Laia, César A. T.
Pina, Fernando
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
UCIBIO - Applied Molecular Biosciences Unit
RUN
dc.contributor.author.fl_str_mv Camuenho, Ambrósio
Jorge Parola, A.
Alejo-Armijo, Alfonso
Pandian, Ramesh
Gomes, Clara S. B.
Laia, César A. T.
Pina, Fernando
dc.subject.por.fl_str_mv Catalysis
Chemistry(all)
Materials Chemistry
topic Catalysis
Chemistry(all)
Materials Chemistry
description UID/QUI/50006/2019. PTDC/QEQ-QFI/1971/2014. PTDC/QUI-COL/32351/2017. PTDC/QUI-QFI/30951/2017. grant no. 219201.
publishDate 2019
dc.date.none.fl_str_mv 2019-01-01
2019-01-01T00:00:00Z
2022-04-02T00:31:03Z
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 http://hdl.handle.net/10362/91641
url http://hdl.handle.net/10362/91641
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1144-0546
PURE: 16445850
https://doi.org/10.1039/c9nj04776j
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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