Structural features of aliphatic N-nitrosamines of 7-azabicyclo[2.2.1]heptanes that facilitate N-NO bond cleavage.
J Am Chem Soc
; 123(42): 10164-72, 2001 Oct 24.
Article
en En
| MEDLINE
| ID: mdl-11603965
ABSTRACT
N-Nitrosamines can be considered as potential nitric oxide (NO)/nitrosonium ion (NO(+)) donors. However, the relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release of NO or NO(+) remains unclear. Here we show that aliphatic N-nitrosoamines of 7-azabicyclo[2.2.1]heptanes can undergo heterolytic N-NO bond cleavage. On the basis of the observation of reduced rotational barriers of the N-NO bonds in solution and nitrogen-pyramidal structures of the N-nitroso group in the solid state, we postulate that N-NO bond cleavage of N-nitrosamines is enhanced by a reduction of the resonance in the N-NO group. Computational studies suggest that these structural features of the N-nitrosamines of 7-azabicyclo[2.2.1]heptane are derived from angle strain imposed on the CNC angles.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos Bicíclicos Heterocíclicos con Puentes
/
Donantes de Óxido Nítrico
/
Nitrosaminas
Idioma:
En
Revista:
J Am Chem Soc
Año:
2001
Tipo del documento:
Article
País de afiliación:
Japón