Application of 13C and 15N spectroscopy to the study of electronic delocalization in N?N bonds: Nitrosamines,hydrazones, triazenes and related protonated species |
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Authors: | J P Gouesnard G J Martin |
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Abstract: | 13C and 15N spectroscopies at natural abundance have been applied to the study of nitrogen lone-pair delocalization in N? N containing compounds: nitrosamines, nitramines, hydrazines, hydrazones and triazenes. Structure-chemical shift correlations have been derived for nitrosamines; the 13C 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 δ15N and of the length of the N? N bond. 15N 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 N? N containing compounds is compared to that of amides. |
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