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Type: Artigo de periódico
Title: Experimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism
Author: Santo, RDD
Simas, RC
Magalhaes, A
dos Santos, VG
Regiani, T
Isler, AC
Martins, NG
Eberlin, MN
Gonzalez, ERP
Abstract: 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 (c) 2013 John Wiley & Sons, Ltd.
Subject: benzoylguanidines
Z isomerism
NMR experiments
ESIMS characterization
Country: EUA
Editor: Wiley-blackwell
Citation: Journal Of Physical Organic Chemistry. Wiley-blackwell, v. 26, n. 4, n. 315, n. 321, 2013.
Rights: fechado
Identifier DOI: 10.1002/poc.3088
Date Issue: 2013
Appears in Collections:Unicamp - Artigos e Outros Documentos

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