Publicação: Experimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism
Carregando...
Data
Orientador
Coorientador
Pós-graduação
Curso de graduação
Título da Revista
ISSN da Revista
Título de Volume
Editor
Tipo
Artigo
Direito de acesso
Acesso restrito
Resumo
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.
Descrição
Palavras-chave
benzoylguanidines, E/Z isomerism, ESI-MS characterization, NMR experiments, Correlation spectroscopy, Electrospray ionization mass spectrometry, Heteronuclear single-quantum coherences, Nuclear overhauser effect spectroscopy, Transform infrared spectroscopy, Bromine compounds, Chlorine compounds, Fourier transform infrared spectroscopy, Mass spectrometry, Molecules, Nitrogen compounds, Nuclear magnetic resonance, Nuclear magnetic resonance spectroscopy, Quantum theory, Stereochemistry, Isomers
Idioma
Inglês
Como citar
Journal of Physical Organic Chemistry, v. 26, n. 4, p. 315-321, 2013.
