Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 1623-1631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201991y
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Funding
- NSF
- ACS-PRF
- NCSA
- Rutgers University
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0953464] Funding Source: National Science Foundation
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The fundamental properties of the parent and substituted 2-pyridones (2-pyridone, 3-chloro-2-pyridone, and 3-formyl-2-pyridone) have been examined in the gas phase using computational and experimental mass spectrometry methods. Newly measured acidities and proton affinities are reported and used to ascertain tautomer preference. These particular substrates (as well as additional 3-substituted pyridones) were chosen in order to examine the correlation between leaving group ability and acidity for moieties that allow resonance delocalization versus those that do not, which is discussed herein.
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