Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides
Autor(a) principal: | |
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Data de Publicação: | 1995 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/1822/72931 |
Resumo: | From a series of Substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied. Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group. In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied. Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.30 V for the sulfonylcarbamates. Small scale electrolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed. For the N-benzylbenzenesulfonamides 1, the pK(a)s in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively. |
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Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamidesScience & TechnologyFrom a series of Substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied. Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group. In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied. Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.30 V for the sulfonylcarbamates. Small scale electrolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed. For the N-benzylbenzenesulfonamides 1, the pK(a)s in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.Royal Society of ChemistryUniversidade do MinhoNyasse, BarthélémyGrehn, LeifRagnarsson, UlfMaia, Hernâni Lopes SilvaMonteiro, Luís S.Leito, Ivo andKoppel, IlmarKoppel, Juta1995-081995-08-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/72931eng1472-778110.1039/P19950002025https://pubs.rsc.org/en/content/articlelanding/1995/P1/p19950002025#!divAbstractinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:40:54Zoai:repositorium.sdum.uminho.pt:1822/72931Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:37:46.674865Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
title |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
spellingShingle |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides Nyasse, Barthélémy Science & Technology |
title_short |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
title_full |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
title_fullStr |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
title_full_unstemmed |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
title_sort |
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides |
author |
Nyasse, Barthélémy |
author_facet |
Nyasse, Barthélémy Grehn, Leif Ragnarsson, Ulf Maia, Hernâni Lopes Silva Monteiro, Luís S. Leito, Ivo and Koppel, Ilmar Koppel, Juta |
author_role |
author |
author2 |
Grehn, Leif Ragnarsson, Ulf Maia, Hernâni Lopes Silva Monteiro, Luís S. Leito, Ivo and Koppel, Ilmar Koppel, Juta |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Nyasse, Barthélémy Grehn, Leif Ragnarsson, Ulf Maia, Hernâni Lopes Silva Monteiro, Luís S. Leito, Ivo and Koppel, Ilmar Koppel, Juta |
dc.subject.por.fl_str_mv |
Science & Technology |
topic |
Science & Technology |
description |
From a series of Substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied. Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group. In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied. Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.30 V for the sulfonylcarbamates. Small scale electrolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed. For the N-benzylbenzenesulfonamides 1, the pK(a)s in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively. |
publishDate |
1995 |
dc.date.none.fl_str_mv |
1995-08 1995-08-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://hdl.handle.net/1822/72931 |
url |
https://hdl.handle.net/1822/72931 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1472-7781 10.1039/P19950002025 https://pubs.rsc.org/en/content/articlelanding/1995/P1/p19950002025#!divAbstract |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799132912757506048 |