Excited-State Triple Proton Transfer of 7-Hydroxyquinoline along a Hydrogen-Bonded Alcohol Chain: Vibrationally Assisted Proton Tunneling

Proton relay in cyclic 7‐hydroxyquinoline–(alcohol)2 complexes (see picture) has been explored in nonpolar solvents. The asymmetric triple proton transfer has an unusually large, temperature‐independent, and viscosity‐dependent kinetic isotope effect. Heavy‐atom motions (wavy arrow) of solvent and b...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-01, Vol.45 (3), p.415-419
Main Authors: Kwon, Oh-Hoon, Lee, Young-Shin, Yoo, Byung Kuk, Jang, Du-Jeon
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Hydrogen Bonding
hydrogen bonds
Hydroxyquinolines - chemistry
isotope effects
Molecular Structure
N heterocycles
proton transfer
Protons
Quantum Theory
time-resolved spectroscopy
Vibration
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Summary:Proton relay in cyclic 7‐hydroxyquinoline–(alcohol)2 complexes (see picture) has been explored in nonpolar solvents. The asymmetric triple proton transfer has an unusually large, temperature‐independent, and viscosity‐dependent kinetic isotope effect. Heavy‐atom motions (wavy arrow) of solvent and bridging molecules allow proton tunneling by assisting the complex to reach the optimal precursor configuration.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503209