Mechanism of the alkaline hydrolysis of O-ethyl S-(2,4,6-trinitrophenyl) thio- and dithiocarbonates

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dc.contributor.authorCastro, EA
dc.contributor.authorCubillos, M
dc.contributor.authorSantos, JG
dc.contributor.authorBujan, EI
dc.contributor.authorRemedi, MV
dc.contributor.authorFernandez, MA
dc.contributor.authorde Rossi, RH
dc.date.accessioned2024-01-10T12:06:36Z
dc.date.available2024-01-10T12:06:36Z
dc.date.issued1999
dc.description.abstractThe alkaline hydrolysis of O-ethyl S-(2,4,6-trinitrophenyl) thio- and dithiocarbonates, 1 and 2, respectively, were studied kinetically in 5% dioxane in water, at 25.0 degrees C, and ionic strength 0.2 mol dm(-3) (KCl). Two kinetic processes, well separated in time, were detected. The fast process involves the formation of a sigma-complex by addition of HO- to one of the unsubstituted positions of the aromatic ring, followed by fast ionisation of this complex. The slow process leads to the formation of a mixture of 2,4,6-trinitrophenoxide and 2,4,6-trinitrobenzenethiolate ions in a 10 : 1 ratio, respectively, in the reaction of 2, and to a mixture in a 2. 1 ratio in the reaction of 1, independent of KOH concentration. Although the substrates show different kinetic behaviour with KOH concentration, the results can be discussed on the basis of a common reaction mechanism.
dc.fechaingreso.objetodigital2024-05-02
dc.format.extent5 páginas
dc.fuente.origenWOS
dc.identifier.doi10.1039/a903143j
dc.identifier.issn0300-9580
dc.identifier.urihttps://doi.org/10.1039/a903143j
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/76182
dc.identifier.wosidWOS:000084992600051
dc.information.autorucQuímica;Castro E;S/I;98722
dc.information.autorucQuímica;Cubillos M;S/I;83695
dc.information.autorucQuímica;Santos JG;S/I;98813
dc.issue.numero11
dc.language.isoen
dc.nota.accesocontenido parcial
dc.pagina.final2607
dc.pagina.inicio2603
dc.publisherROYAL SOC CHEMISTRY
dc.revistaJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
dc.rightsacceso restringido
dc.subjectNUCLEOPHILIC AROMATIC-SUBSTITUTION
dc.subjectSINGLE-ELECTRON TRANSFER
dc.subjectSIGMA-ADDUCT FORMATION
dc.subjectCONCERTED MECHANISM
dc.subjectLEAVING GROUPS
dc.subjectKINETICS
dc.subjectAMINOLYSIS
dc.subjectAMINES
dc.subjectTHIOCARBONATE
dc.subject2,4-DINITROPHENYL
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleMechanism of the alkaline hydrolysis of O-ethyl S-(2,4,6-trinitrophenyl) thio- and dithiocarbonates
dc.typeartículo
sipa.codpersvinculados98722
sipa.codpersvinculados83695
sipa.codpersvinculados98813
sipa.indexWOS
sipa.trazabilidadCarga SIPA;09-01-2024
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