Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study

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dc.creatorJodieh Varejão
dc.creatorLuiz Cláudio de Almeida Barbosa
dc.creatorEduardo Varejão
dc.creatorAline Souza
dc.creatorMateus Lage
dc.creatorJosé Carneiro
dc.date.accessioned2023-10-09T23:08:01Z
dc.date.accessioned2025-09-09T00:49:32Z
dc.date.available2023-10-09T23:08:01Z
dc.date.issued2020
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipFAPERJ - Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.21577/0103-5053.20190131
dc.identifier.issn0103-5053
dc.identifier.urihttps://hdl.handle.net/1843/59329
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectQuímica
dc.subjectFuncionais de densidade
dc.subject.otherNostoclide
dc.subject.otherZ-E isomerization
dc.subject.otherγ-lactone
dc.subject.otherDFT calculations
dc.subject.otherButenolides
dc.subject.otherAcid catalysis
dc.titleAcid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study
dc.typeArtigo de periódico
local.citation.epage99
local.citation.issue1
local.citation.spage90
local.citation.volume31
local.description.resumoThe Z-E isomerization of γ-alkylidenebutenolide analogues to natural nostoclides and other natural butenolides was investigated using 1H nuclear magnetic resonance (NMR) and high performance liquid chromatography (HPLC) data as well as density functional theory (DFT) calculations at the wB97x-D/6-31G(d,p) level, including solvent effects with the polarizable continuum solvation approach. The experimental data supported the Z to E isomerization of γ-alkylidenebutenolides under acid catalysis. Newly prepared samples have predominantly Z configuration, which partially isomerizes to the E isomer under acidic conditions. Density functional theory studies corroborate the experimental findings. While neutral γ-alkylidenebutenolides are more stable in the Z form, protonation of the γ-lactone carbonyl group results in preferential stabilization of the E isomer.
local.identifier.orcidhttps://orcid.org/0000-0002-5395-9608
local.identifier.orcidhttps://orcid.org/0000-0002-3491-1764
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.scielo.br/j/jbchs/a/m7Z34BSjLJ8WBnSBKfsS8zG/abstract/?lang=en

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