Campus Units
Chemistry
Document Type
Book Chapter
Publication Version
Published Version
Publication Date
7-23-2009
Journal or Book Title
Structure and Reactivity in Aqueous Solution
Volume
568
Issue
ACS Symposium Series
First Page
182
Last Page
195
DOI
10.1021/bk-1994-0568.ch013
Abstract
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.
Copyright Owner
American Chemical Society
Copyright Date
1994
Language
en
File Format
application/pdf
Recommended Citation
Gai, F.; Rich, R. L.; Chen, Y.; and Petrich, Jacob W., "Probing Solvation by Alcohols and Water with 7-Azaindole" (2009). Chemistry Publications. 815.
https://lib.dr.iastate.edu/chem_pubs/815
Comments
Reprinted (adapted) with permission from Structure and Reactivity in Aqueous Solution, ACS Symposium Series, Vol. 568, Chapter 13 (1994): 182, doi: 10.1021/bk-1994-0568.ch013. Copyright 1994 American Chemical Society.