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Review | Regular issue | Vol 19, No. 1, 1982, pp.93-109
Published online, 1st January, 1970
DOI: 10.3987/R-1982-01-0093
Backdonation and Interrelationships between 15N, 13C Chemical Shifts and Infrared Absorption Frequencies in Heterocyclic N-Oxides

William W. Paudler and Misa V. Jovanovic

*Department of Chemistry, Portland State University, Portland, Oregon 97207, U.S.A.


1) A relationship has been shown to exist between the 15N chemical shifts of a number of N-oxides and their υNO absorption frequencies.
2) A similar relationship exists between the σNO ionization potentials of N-oxides and their υNO absorption frequencies.
3) The changes in 15N chemical shifts of these N-oxides are reflected in changes of the 13C chemical shifts of the carbons α to the N-oxide function.
4) By comparing the 15N chemical shift changes of the N-oxides and their oxygen protonated analogs, a measure of the extent of backdonation, relatable to the π-deficiency of the N-oxides, has been established.
5) The steric inhibition to backdonation in some appropriately di-substituted N-oxides has been estimated by means of their υNO frequencies and changes in the 13C chemical shifts of the α-carbons.