The nucleophilicity N index in organic chemistry

Luis R. Domingo, Patricia Pérez

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

283 Citas (Scopus)

Resumen

The nucleophilicity N index (J. Org. Chem.2008, 73, 4615), the inverse of the electrophilicity, and the recently proposed inverse of the electrodonating power, (J. Org. Chem.2010, 75, 4957) have been checked toward (i) a series of single 5-substituted indoles for which rate constants are available, (ii) a series of para-substituted phenols, and for (iii) a series of 2,5-disubstituted bicyclic[2.2.1]hepta-2,5-dienes which display concurrently electrophilic and nucleophilic behaviors. While all considered indices account well for the nucleophilic behavior of organic molecules having a single substitution, the nucleophilicity N index works better for more complex molecules. Unlike, the inverse of the electrophilicity, (R 2 = 0.71), and the inverse of the electrodonating power, (R 2 = 0.83), a very good correlation of the nucleophilicity N index of twelve 2-substituted-6-methoxy-bicyclic[2.2.1]hepta- 2,5-dienes versus the activation energy associated with the nucleophilic attack on 1,1-dicyanoethylene is found (R 2 = 0.99). This comparative study allows to assert that the nucleophilicity N index is a measure of the nucleophilicity of complex organic molecules displaying concurrently electrophilic and nucleophilic behaviors.

Idioma originalInglés
Páginas (desde-hasta)7168-7175
Número de páginas8
PublicaciónOrganic and Biomolecular Chemistry
Volumen9
N.º20
DOI
EstadoPublicada - 21 oct 2011

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Química física y teórica
  • Química orgánica

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