Photo-pK of indoline-2-thione

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dc.contributor.authorAraya-Hernández, Carmen Gloriadeu
dc.contributor.authorSteiner, Ulrich
dc.date.accessioned2011-03-24T18:13:32Zdeu
dc.date.available2011-03-24T18:13:32Zdeu
dc.date.issued2005deu
dc.description.abstractThe photochemistry and photokinetics of indoline-2-thione (1) has been investigated by continuous illumination at 334 nm and flash photolysis in aqueous solutions as a function of pH. The photokinetic behaviour and product distribution were almost independent on the presence of oxygen in the solution. Whereas indole is formed as the main product in acidic solutions biindolyl was found as the main product in unbuffered solution. For the quantum yield f of photodegradation of 1 a marked increase was observed in acidic solutions. The pH dependence follows a Henderson-Hasselbalch relation with a pKa of 2.2. This photo-pK does note correspond to a pKa in the ground state. It is tentatively assigned to the protolytic equilibrium 3 1 + H+ → 3 1H+ in the excited triplet state, evidence for which is found in the pH-dependence of transient absorption observed in laser flash photolysis experiments. Our findings support the intermediacy of a 2-mercapto-indole tautomer of 1 in the photochemical desulfurization mechanism as suggested previously by Nishio.11eng
dc.description.versionpublished
dc.format.mimetypeapplication/pdfdeu
dc.identifier.citationFirst publ. in: Journal of the Chilean Chemical Society 50 (2005), 2, pp. 505-511deu
dc.identifier.doi10.4067/S0717-97072005000200013
dc.identifier.ppn27759006Xdeu
dc.identifier.urihttp://kops.uni-konstanz.de/handle/123456789/9664
dc.language.isoengdeu
dc.legacy.dateIssued2008deu
dc.rightsAttribution-NonCommercial-NoDerivs 2.0 Generic
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/2.0/
dc.subject.ddc540deu
dc.titlePhoto-pK of indoline-2-thioneeng
dc.typeJOURNAL_ARTICLEdeu
dspace.entity.typePublication
kops.citation.bibtex
@article{ArayaHernandez2005Photo-9664,
  year={2005},
  doi={10.4067/S0717-97072005000200013},
  title={Photo-pK of indoline-2-thione},
  number={2},
  volume={50},
  journal={Journal of the Chilean Chemical Society},
  pages={505--511},
  author={Araya-Hernández, Carmen Gloria and Steiner, Ulrich}
}
kops.citation.iso690ARAYA-HERNÁNDEZ, Carmen Gloria, Ulrich STEINER, 2005. Photo-pK of indoline-2-thione. In: Journal of the Chilean Chemical Society. 2005, 50(2), pp. 505-511. eISSN 0717-9707. Available under: doi: 10.4067/S0717-97072005000200013deu
kops.citation.iso690ARAYA-HERNÁNDEZ, Carmen Gloria, Ulrich STEINER, 2005. Photo-pK of indoline-2-thione. In: Journal of the Chilean Chemical Society. 2005, 50(2), pp. 505-511. eISSN 0717-9707. Available under: doi: 10.4067/S0717-97072005000200013eng
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