Probing Solvation by Alcohols and Water with 7-Azaindole

dc.contributor.author Gai, F.
dc.contributor.author Rich, R.
dc.contributor.author Petrich, Jacob
dc.contributor.author Chen, Y.
dc.contributor.author Petrich, Jacob
dc.contributor.department Chemistry
dc.date 2018-02-17T09:24:16.000
dc.date.accessioned 2020-06-30T01:23:07Z
dc.date.available 2020-06-30T01:23:07Z
dc.date.copyright Sat Jan 01 00:00:00 UTC 1994
dc.date.issued 2009-07-23
dc.description.abstract <p>The nonradiative pathways of 7-azaindole are extremely sensitive to solvent. In alcohols, 7-azaindole executes an excited-state double-proton transfer. In water, this tautomerization is frustrated. Proton inventory experiments suggest a concerted double-proton transfer in the alcohols and point to another nonradiative process in water. We propose the following idealized picture. Whereas at room temperature 7-azaindole can form a cyclic hydrogen-bonded intermediate with a single alcohol molecule facilitating tautomerization, in water more than one solvent molecule coordinates to the solute and thus prohibits the concerted process. More detailed measurements, however, indicate that water and alcohols do not solvate 7-azaindole in fundamentally different ways, but rather that they represent two extremes of the same phenomenon.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>Structure and Reactivity in Aqueous Solution</em>, ACS Symposium Series, Vol. 568, Chapter 13 (1994): 182, doi: <a href="http://dx.doi.org/10.1021/bk-1994-0568.ch013" target="_blank">10.1021/bk-1994-0568.ch013</a>. Copyright 1994 American Chemical Society.</p>
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dc.identifier archive/lib.dr.iastate.edu/chem_pubs/815/
dc.identifier.articleid 1786
dc.identifier.contextkey 7965949
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/815
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/15309
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/815/0-1994_PetrichJW_StructureReactivityAqueous.pdf|||Sat Jan 15 02:07:10 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/815/1994_PetrichJW_ProbingSolvationAlcohols.pdf|||Sat Jan 15 02:07:11 UTC 2022
dc.source.uri 10.1021/bk-1994-0568.ch013
dc.subject.disciplines Chemistry
dc.title Probing Solvation by Alcohols and Water with 7-Azaindole
dc.type article
dc.type.genre book_chapter
dspace.entity.type Publication
relation.isAuthorOfPublication 563e8d72-b6e9-4617-91c0-589d263e00fc
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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