Application of 13C and 15N spectroscopy to the study of electronic delocalization in NN bonds: Nitrosamines, hydrazones, triazenes and related protonated species
✍ Scribed by J. P. Gouesnard; G. J. Martin
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- English
- Weight
- 755 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
^13^C and ^15^N spectroscopies at natural abundance have been applied to the study of nitrogen lone‐pair delocalization in NN containing compounds: nitrosamines, nitramines, hydrazines, hydrazones and triazenes. Structure‐chemical shift correlations have been derived for nitrosamines; the ^13^C upfield effect of a γ substituent has been used for assigning the configuration of both diastereoisomers in N,N‐unsymmetrically substituted nitrosamines. Equations have been computed which permit the prediction of the electronic delocalization, expressed in terms of free enthalpy of activation ΔG, as a function of δ^15^N and of the length of the NN bond. ^15^N spectroscopy has also been applied to the study of the protonated species of nitrosamines and of acceptor‐donor complexes of nitrosamines with Lewis acids. The behaviour of such NN containing compounds is compared to that of amides.