Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/326132
Type: Artigo
Title: Theoretical And Nmr Experimental Insights On Urea, Thiourea And Diindolyurea As Fluoride Carriers
Author: Mendonca
Joao Guilherme P.; Silla
Josue M.; Andrade
Laize A. F.; Fernandes
Sergio A.; Cormanich
Rodrigo A.; Freitas
Matheus P.
Abstract: Urea and thiourea derivatives are widely known as anion transporters. The pristine urea and thiourea compounds were theoretically and spectroscopically evaluated as fluoride ligands, since transportation of F- is involved in many biochemical processes and this anion is suitable to be analyzed through NMR. Conformational changes induced by anions can be useful to probe ligand-anion complexation, but urea and thiourea do not undergo conformational isomerization. Thus, diindolylurea (DIU) was computationally investigated to search for its conformational preferences upon complexation with fluoride. Overall, the NMR proton signal for urea and thiourea moved downfield and broadened upon addition of one equivalent of fluoride anion in DMSO solution, indicating complexation. The F-19 signal for the thiourea-F- mixture also shifted relative to the anion source. However, a J((N)H,F) coupling constant was not observed, probably because of entropy and bulk salvation effects. In addition, the conformational preference of DIU changed drastically after simulated complexation with fluoride, in agreement with previous studies with other anions. This confirms the potential of urea derivatives as fluoride carriers. (C) 2016 Elsevier B.V. All rights reserved.
Subject: Conformational Analysis
Anion Transporters
Fluoride
Nmr
Theoretical Calculations
Editor: Elsevier Science BV
Amsterdam
Rights: fechado
Identifier DOI: 10.1016/j.molstruc.2016.02.052
Address: http://www-sciencedirect-com.ez88.periodicos.capes.gov.br/science/article/pii/S0022286016301454
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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