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The effect of 4‐substituents on the stability of pyridinium dicarbethoxymethylides
Author(s) -
Douglass James K.,
Tabor M. Wilson,
Spradling Julius E.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090108
Subject(s) - pyridinium , chemistry , substituent , intramolecular force , pyridine , spectral line , pyridinium compounds , charge (physics) , computational chemistry , chemical stability , medicinal chemistry , photochemistry , crystallography , stereochemistry , organic chemistry , physics , quantum mechanics , astronomy
The effect of 4‐substituents on the stability of pyridinium dicarbethoxymethylides, as determined by p K a measurements, is found to correlate well with their effect on the stability of similarly substituted pyridine 1‐oxides. Displacements in chemical shift in the ylides, particularly of the α‐protons, are also found to correlate well with substituent effects. Intramolecular charge‐transfer transitions in the electronic spectra, characteristic of pyridinium ylides, are reported.