Detailed 1H and 13C NMR Spectral Data Assignment for Two Dihydrobenzofuran Neolignans

Author(s)

Talita C. T. Medeiros ^[1] ; Herbert J. Dias ^[2] ; Eliane O. Silva ^[3] ; Murilo J. Fukui ^[4] ; Ana Carolina F. Soares ^[5] ; Tapas Kar ^[6] ; Vladimir C. G. Heleno ^[7] ; Paulo M. Donate ^[8] ; Renato L. T. Parreira ^[9] ; Antônio E. M. Crotti ^[10]

Affiliation

^[1] Universidade de São Paulo. Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto. Departamento de Química - Brasil

^[2] Universidade de São Paulo. Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto. Departamento de Química - Brasil

^[3] Universidade de São Paulo. Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto. Departamento de Química - Brasil

^[4] Universidade de Franca. Núcleo de Pesquisas em Ciências Exatas e Tecnológicas - Brasil

^[5] Universidade de Franca. Núcleo de Pesquisas em Ciências Exatas e Tecnológicas - Brasil

^[6] Utah State University. Department of Chemistry and Biochemistry - Estados Unidos

^[7] Universidade de Franca. Núcleo de Pesquisas em Ciências Exatas e Tecnológicas - Brasil

^[8] Universidade de São Paulo. Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto. Departamento de Química - Brasil

^[9] Universidade de Franca. Núcleo de Pesquisas em Ciências Exatas e Tecnológicas - Brasil

^[10] Universidade de São Paulo. Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto. Departamento de Química - Brasil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 27, n. 1, p. 136-143, 2016-01-00.

Abstract

In this work we present a complete proton (1H) and carbon 13 (13C) nuclear magnetic resonance (NMR) spectral analysis of two synthetic dihydrofuran neolignans (±)-trans-dehydrodicoumarate dimethyl ester and (±)-trans-dehydrodiferulate dimethyl ester. Unequivocal assignments were achieved by 1H NMR, proton decoupled 13C (13C{1H}) NMR spectra, gradient-selected correlation spectroscopy (gCOSY), J-resolved, gradient-selected heteronuclear multiple quantum coherence (gHMQC), gradient-selected heteronuclear multiple bond coherence (gHMBC) and nuclear Overhauser effect spectroscopy (NOESY) experiments. All hydrogen coupling constants were measured, clarifying all the hydrogen signals multiplicities. Computational methods were also used to simulate the 1H and 13C chemical shifts and showed good agreement with the trans configuration of the substituents at C7 and C8. (AU)

• FAPESP's process: 09/12202-1 - Antischistosomal and antileishmanial in vitro activities of some dihydrobenzofuran lignans
• Grantee: Murilo de Jesus Fukui
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 11/07623-8 - The use of quantum-mechanical methods to study the bonds and chemical interactions in self-organizing systems with applications in catalysis, medicinal chemistry, electrochromism, energy storage and conversion
• Grantee: Renato Luis Tame Parreira
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 13/20094-0 - Evaluation of the anti-parasitary and insecticidal activities of benzofuran derivatives, and study of their gas-phase fragmentation reactions using tandem mass spectrometry
• Grantee: Antônio Eduardo Miller Crotti
• Support Opportunities: Regular Research Grants