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ESR, electrochemical and cyclodextrin-inclusion studies of triazolopyridyl pyridyl ketones and dipyridyl ketones derivatives

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2008-11
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Olea Azar, Claudio
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ESR, electrochemical and cyclodextrin-inclusion studies of triazolopyridyl pyridyl ketones and dipyridyl ketones derivatives
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Author
  • Olea Azar, Claudio;
  • Abarca, B.;
  • Norambuena, Ester;
  • Opazo, L.;
  • Jullian Matthaei, Carolina;
  • Valencia, S.;
  • Ballesteros, R.;
  • Chadlaoui, M.;
Abstract
The electron spin resonance (ESR) spectra of free radicals obtained by electrolytic reduction of triazolopyridyl pyridyl ketones and dipyridyl ketones derivatives were measured in dimethylsulfoxide (DMSO). The hyperfine patterns indicate that the spin density delocalization is dependent of the rings presented in the molecule. The electrochemistry of these compounds was characterized using cyclic voltammetry, in DMSO as solvent. When one carbonyl is present in the molecule one step in the reduction mechanism was observed while two carbonyl are present two steps were detected. The first wave was assigned to the generation of the correspondent free radical species, and the second wave was assigned to the dianion derivatives. The phase–solubility measurements indicated an interaction between molecules selected and cyclodextrins in water. These inclusion complexes are 1:1 with CD, and HP- CD. The values of Ks showed a different kind of complexes depending on which rings are included. AM1 and DFT calculations were performed to obtain the optimized geometries, theoretical hyperfine constants, and spin distributions, respectively. The theoretical results are in complete agreement with the experimental ones.
Patrocinador
Our thanks are due to the Ministerio de Educaci´on y Ciencia Project CTQ 2006-15672-C05-03/BQC and Vicerrectorado de Relaciones Internacionales de la Universidad de Valencia for a grant to C.O.-A.
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URI: https://repositorio.uchile.cl/handle/2250/120838
ISSN: 1386-1425
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Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Volume 71, Issue 2, 2008, Pages 703-709
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