Experimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism
Data de publicação2013-04-01
Direito de acesso
MetadadosExibir registro completo
Molecules containing the guanidinic nuclei possess several pharmacological applications, and knowing the preferred isomers of a potential drug is important to understand the way it operates pharmacologically. Benzoylguanidines were synthesized in satisfactory to good yields and characterized by NMR, Electrospray Ionization Mass Spectrometry (ESI-MS) and Fourrier Transform InfraRed Spectroscopy techniques (FTIR). E/Z isomerism of the guanidines was studied and confirmed by NMR analysis in solution (1H-13C Heteronuclear Single Quantum Coherence (HSQC) and Heteronuclear Multiple-Bond Correlation (HMBC), 1H-15N HMBC, 1H- 1H Correlation Spectroscopy (COSY) and Nuclear Overhauser Effect Spectroscopy (NOESY) experiments) at low temperatures. Compounds with p-Cl and p-Br aniline moiety exist mainly as Z isomer with a small proportion of E isomer, whereas compounds with p-NO2 moiety showed a decrease in proportion of isomer Z. The results are important for the application of these molecules as enzymatic inhibitors. Copyright © 2013 John Wiley & Sons, Ltd.
Como citar este documento
Este item aparece nas seguintes coleções
Exibindo os itens relacionados pelo título, autor e palavra-chave.
Moraes, João Carlos Silos ; Carelli, G.; Moretti, A.; Moruzzi, G.; Strumia, F. (Journal of Molecular Spectroscopy, 1998) [Artigo]The Ritz computer program, developed for facilitating the assignment of molecular Fourier transform absorption spectra and described in a previous work, determines the energy level values involved in the assigned transitions ...
Suicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate Orth, Elisa S.; Da Silva, Pedro L. F.; Mello, Renata S.; Bunton, Clifford A.; Milagre, Humberto M. S. ; Eberlin, Marcos N.; Fiedler, Haidi D.; Nome, Faruk (Journal of Organic Chemistry, 2009) [Artigo](Chemical Equation Presented) The reaction between the benzohydroxamate anion (BHO-) and bis(2,4-dinitrophenyl)phosphate (BDNPP) has been examined kinetically, and the products were characterized by mass and NMR spectroscopy. ...
Ultra-structural mapping of sugarcane bagasse after oxalic acid fiber expansion (OAFEX) and ethanol production by Candida shehatae and Saccharomyces cerevisiae Chandel, Anuj K.; Antunes, Felipe F. A.; Anjos, Virgilio; Bell, Maria J. V.; Rodrigues, Leonarde N.; Singh, Om V.; Rosa, Carlos A.; Pagnocca, Fernando C. ; Da Silva, Silvio S. (Biotechnology for Biofuels, 2013) [Artigo]Background: Diminishing supplies of fossil fuels and oil spills are rousing to explore the alternative sources of energy that can be produced from non-food/feed-based substrates. Due to its abundance, sugarcane bagasse ...