Please use this identifier to cite or link to this item: https://hdl.handle.net/10216/82114
Full metadata record
DC FieldValueLanguage
dc.creatorGomes, JRB
dc.creatorGomes, P
dc.date.accessioned2022-09-13T23:48:17Z-
dc.date.available2022-09-13T23:48:17Z-
dc.date.issued2005
dc.identifier.issn0040-4020
dc.identifier.othersigarra:89122
dc.identifier.urihttps://hdl.handle.net/10216/82114-
dc.description.abstractA computational study at the density functional theory level was performed on bioactive and model sulfonamides with the aim of determining the factors affecting the acidity of the sulfonamido group. The effects of introducing different substiments at either the para-aryl or the N-1-sulfonamide positions were independently analyzed. A linear correlation was found between sulfonamide acidity and the Hammett constants or charge of the SO2 group of substituents at the para-aryl position. Most N-1-substituents were taken from bacteriostatic sulfonamide structures and presented a more complex behavior, possibly due to a conjugation of steric and electronic factors. In the latter situation, sulfonamide acidity and the charge of the SO2 group were not linearly correlated. Interestingly, the acidity of the sulfonamido group was found to be correlated with the reactivity of sulfa drugs towards acylating agents. The implications for the design of suitable sulfonamide prodrugs are discussed.
dc.language.isoeng
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc/4.0/
dc.subjectQuímica
dc.subjectChemical sciences
dc.titleGas-phase acidity of sulfonamides: implications for reactivity and prodrug design
dc.typeArtigo em Revista Científica Internacional
dc.contributor.uportoFaculdade de Ciências
dc.identifier.doi10.1016/j.tet.2005.01.034
dc.identifier.authenticusP-000-49T
dc.subject.fosCiências exactas e naturais::Química
dc.subject.fosNatural sciences::Chemical sciences
Appears in Collections:FCUP - Artigo em Revista Científica Internacional

Files in This Item:
File Description SizeFormat 
89122.pdf308.92 kBAdobe PDFThumbnail
View/Open


This item is licensed under a Creative Commons License Creative Commons