Reaction of OH radicals with 2- and 4-pyridones in aqueous solution. An electron spin resonance and pulse radiolysis study

Journal Article · Thu Sep 06 00:00:00 EDT 1979 · J. Phys. Chem.; (United States)

DOI:https://doi.org/10.1021/j100481a021· OSTI ID:6014867

Steenken, S ^[1]; O'Neill, P

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1. Max-Planck-Institut fuer Kohlenforschung, Muelheim, Germany

OH radicals react with 2- and 4-pyridone (k = 4.4 x 10/sup 9/ and 3.6 x 10/sup 9/M/sup -1/s/sup -1/, respectively) and with 2- and 4-pyridonecarboxylic acids by preferential attachment to the 3 or 5 position of the pyridone ring. With the exception of 4-pyridone-2,6-dicarboxylic acid, the OH adducts thus formed undergo keto-enol tautomerization to yield OH adducts of the pyridol type (k greater than or equal to 10/sup 3/s/sup -1/). At pH greater than or equal to 10 the OH adducts deprotonate to yield the corresponding radical anions. The ionized OH adduct of 4-pyridone eliminates OH/sup -/(k = 1.8 x 10/sup 4/s/sup -1/) to yield the pyridin-4-oxyl radical which is able to oxidize ascorbate. The pyridin-4-oxyl radical can also be obtained from the OH adduct of 4-pyridone by H/sup +/ assisted dehydration (k = 2.5 x 10/sup 6/M/sup -1/s/sup -1/). Corresponding reactions involving the OH adduct of 2-pyridone were not observed.

• OSTI ID: 6014867
• Journal Information: J. Phys. Chem.; (United States), Journal Name: J. Phys. Chem.; (United States) Vol. 83:18; ISSN JPCHA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400600* -- Radiation Chemistry
AZINES
CHEMICAL RADIATION EFFECTS
CHEMICAL REACTIONS
CHEMISTRY
DATA
DATA FORMS
DECOMPOSITION
ELECTRON SPIN RESONANCE
ELECTRONS
ELEMENTARY PARTICLES
EXPERIMENTAL DATA
FERMIONS
HETEROCYCLIC COMPOUNDS
HYDROXYL RADICALS
INFORMATION
ISOLATED VALUES
KETONES
LEPTONS
MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIDINES
RADIATION CHEMISTRY
RADIATION EFFECTS
RADICALS
RADIOLYSIS
RESONANCE