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Effect of nitrogen substituents on C—N rotational barriers in enamine derivatives (1985)

Azzaro, Marcel ; Geribaldi, Serge ; Videau, Bruno

Chichester : Wiley-Blackwell

Organic Magnetic Resonance 23 (1985), S. 28-32

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ISSN: 0749-1581

Keywords: Chemistry ; Analytical Chemistry and Spectroscopy

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Rates of rotation around the C—N bond in a series of ten N,N-disubstituted 3-amino-5,5-dimethylcyclohex-2-enones were determined from total NMR line shape analysis. Linear correlations are shown to exist between Δ298≠ and parameters describing the inductive and steric effects of N-alkyl substituents. The substituent effects on the barriers seem to occur mainly through a change in the potential energy of non-bonded interactions between the nitrogen substituents and the hydrogen atoms in the ortho position to the amino group.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/mrc.1260230110

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