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Experimental NMR and MS study of benzoylguanidines. Investigation of E / Z isomerism
Author(s) -
Santo Rafael Dias do Espírito,
Simas Rosineide Costa,
Magalhães Alviclér,
Santos Vanessa Gonçalves dos,
Regiani Thais,
Isler Ana Cristina,
Martins Natiza Graziele,
Eberlin Marcos Nogueira,
González Eduardo René Pérez
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3088
Subject(s) - chemistry , heteronuclear single quantum coherence spectroscopy , heteronuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , moiety , electrospray ionization , molecule , spectroscopy , nuclear magnetic resonance spectroscopy , mass spectrometry , nuclear overhauser effect , carbon 13 nmr , stereochemistry , aniline , computational chemistry , organic chemistry , chromatography , physics , quantum mechanics
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 ( 1 H‐ 13 C Heteronuclear Single Quantum Coherence (HSQC) and Heteronuclear Multiple‐Bond Correlation (HMBC), 1 H‐ 15 N HMBC, 1 H‐ 1 H 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.