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Article
Ionization in Liquid Ammonia of Methyl and Amino Groups Bonded to Pyridine and Pyrazine. A Method of Determining Their pKa Values
Journal of Organic Chemistry
  • John A. Zoltewic
  • Larry S. Helmick, Cedarville University
Document Type
Article
Publication Date
1-1-1973
Abstract
Proton magnetic resonance spectra of ionized 2-methyl and 2-amino derivatives of pyridine and pyrazine along with spectra of 2-pyridone and 2-pyrazinone in liquid ammonia are reported. Changes in chemical shifts produced by ionization of the pyridines are linearly related to those for the pyrazines. Competition experiments show that 2-methyl- is less acidic than 4-methylpyridine; estimates of the pK, values for these two acids are given. It is suggested that the results provide a basis for determining the equilibrium acidities of weak heterocyclic acids.
Disciplines
Keywords
  • ionization,
  • liquid ammonia,
  • pyridine,
  • pyrazine
Citation Information
Helmick, L. S. (1973). Ionization in Liquid Ammonia of Methyl and Amino Groups Bonded to Pyridine and Pyrazine. A Method of Determining Their pKa Values. Journal of Organic Chemistry, 38, 658-662.