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Type:	Artigo de Periódico
Title:	Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study
Authors:	Jodieh Varejão Luiz Cláudio de Almeida Barbosa Eduardo Varejão Aline Souza Mateus Lage José Carneiro
Abstract:	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.
Subject:	Química Funcionais de densidade
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 Aberto
metadata.dc.identifier.doi:	https://doi.org/10.21577/0103-5053.20190131
URI:	http://hdl.handle.net/1843/59329
Issue Date:	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
Appears in Collections:	Artigo de Periódico

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