Tert‐butyl hydroperoxide‐promoted guanylation of amines with benzoylthioureas: mechanistic insights by HRMS and 1H NMR

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dc.creatorHenrique Esteves
dc.creatorTiago Oliveira Brito
dc.creatorRenato Ribeiro-Viana
dc.creatorÂngelo de Fátima
dc.creatorFernando César de Macedo Júnior
dc.date.accessioned2024-07-25T19:37:44Z
dc.date.accessioned2025-09-08T23:14:30Z
dc.date.available2024-07-25T19:37:44Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1002/poc.3698
dc.identifier.issn0894-3230
dc.identifier.urihttps://hdl.handle.net/1843/71506
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Physical Organic Chemistry
dc.rightsAcesso Restrito
dc.subjectQuímica
dc.subjectEspectrometria de massa
dc.subjectRessonância magnética nuclear
dc.subjectGuanidina
dc.subjectAminas
dc.subjectReação nucleofilica
dc.subjectTiouréia - Oxidação
dc.subjectCinética química
dc.subject.otherGuanylation
dc.subject.otherTerc-Butyl hydroxyperoxide
dc.subject.otherThiourea oxidation
dc.subject.otherMass spectrometry
dc.titleTert‐butyl hydroperoxide‐promoted guanylation of amines with benzoylthioureas: mechanistic insights by HRMS and 1H NMR
dc.typeArtigo de periódico
local.citation.epage50
local.citation.issue12
local.citation.spage43
local.citation.volume30
local.description.resumoHerein, we present a mechanistic study on tert‐butyl hydroperoxide‐promotedguanylation of thioureas by monitoring short lifetime intermediates using electrosprayionisation/time‐of‐flight high resolution mass spectrometry (ESI‐Q‐TOF HRMS).Moreover, 1H nuclear magnetic resonance data allowed us to access kinetic parametersfor the main species involved which, allied to the HRMS results, furnished valuableinsights over previously reported observations. The results suggested an addition/elimina-tion mechanism involving the aminoiminomethanesulphinic acid, RNC(SO2H)NHR′,and the nucleophilic amine as the main pathway to yield the guanidine. Noteworthy,benzoylthiourea consumption rate presented a nonlinear kinetic behaviour, while tBuOOHand the nucleophilic amine consumptions were found to follow second‐order kinetics.
local.identifier.orcidhttps://orcid.org/0000-0002-2247-8334
local.identifier.orcidhttps://orcid.org/0000-0002-5036-9995
local.identifier.orcidhttps://orcid.org/0000-0001-6603-4770
local.identifier.orcidhttps://orcid.org/0000-0002-4230-1309
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/org/science/article/abs/pii/S0894323022010967

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