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http://hdl.handle.net/1843/59329| Tipo: | Artigo de Periódico |
| Título: | Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study |
| Autor(es): | Jodieh Varejão Luiz Cláudio de Almeida Barbosa Eduardo Varejão Aline Souza Mateus Lage José Carneiro |
| Resumen: | The 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. |
| Asunto: | Química Funcionais de densidade |
| Idioma: | eng |
| País: | Brasil |
| Editor: | Universidade Federal de Minas Gerais |
| Sigla da Institución: | UFMG |
| Departamento: | ICX - DEPARTAMENTO DE QUÍMICA |
| Tipo de acceso: | Acesso Aberto |
| Identificador DOI: | https://doi.org/10.21577/0103-5053.20190131 |
| URI: | http://hdl.handle.net/1843/59329 |
| Fecha del documento: | 2020 |
| metadata.dc.url.externa: | https://www.scielo.br/j/jbchs/a/m7Z34BSjLJ8WBnSBKfsS8zG/abstract/?lang=en |
| metadata.dc.relation.ispartof: | Journal of the Brazilian Chemical Society |
| Aparece en las colecciones: | Artigo de Periódico |
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| Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides_ An Experimental and DFT Study.pdf | 679.19 kB | Adobe PDF | Visualizar/Abrir |
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