Experimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism

dc.contributorUniversidade Estadual Paulista (UNESP)
dc.creatorSanto, Rafael Dias Do Espírito
dc.creatorSimas, Rosineide Costa
dc.creatorMagalhães, Alviclér
dc.creatorSantos, Vanessa Gonçalves Dos
dc.creatorRegiani, Thais
dc.creatorIsler, Ana Cristina
dc.creatorMartins, Natiza Graziele
dc.creatorEberlin, Marcos Nogueira
dc.creatorGonzález, Eduardo René Pérez
dc.date2014-05-27T11:28:44Z
dc.date2016-10-25T18:45:56Z
dc.date2014-05-27T11:28:44Z
dc.date2016-10-25T18:45:56Z
dc.date2013-04-01
dc.date.accessioned2017-04-06T02:17:46Z
dc.date.available2017-04-06T02:17:46Z
dc.identifierJournal of Physical Organic Chemistry, v. 26, n. 4, p. 315-321, 2013.
dc.identifier0894-3230
dc.identifier1099-1395
dc.identifierhttp://hdl.handle.net/11449/74896
dc.identifierhttp://acervodigital.unesp.br/handle/11449/74896
dc.identifier10.1002/poc.3088
dc.identifierWOS:000316755800006
dc.identifier2-s2.0-84875496782
dc.identifierhttp://dx.doi.org/10.1002/poc.3088
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/895655
dc.descriptionMolecules 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.
dc.languageeng
dc.relationJournal of Physical Organic Chemistry
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectbenzoylguanidines
dc.subjectE/Z isomerism
dc.subjectESI-MS characterization
dc.subjectNMR experiments
dc.subjectCorrelation spectroscopy
dc.subjectElectrospray ionization mass spectrometry
dc.subjectHeteronuclear single-quantum coherences
dc.subjectNuclear overhauser effect spectroscopy
dc.subjectTransform infrared spectroscopy
dc.subjectBromine compounds
dc.subjectChlorine compounds
dc.subjectFourier transform infrared spectroscopy
dc.subjectMass spectrometry
dc.subjectMolecules
dc.subjectNitrogen compounds
dc.subjectNuclear magnetic resonance
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectQuantum theory
dc.subjectStereochemistry
dc.subjectIsomers
dc.titleExperimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism
dc.typeOtro


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