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Issue 20, 2011
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The nucleophilicity N index in organic chemistry

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Abstract

The nucleophilicity N index (J. Org. Chem.2008, 73, 4615), the inverse of the electrophilicity, Image ID:c1ob05856h-t1.gif, and the recently proposed inverse of the electrodonating power, Image ID:c1ob05856h-t2.gif, (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, Image ID:c1ob05856h-t3.gif, (R2 = 0.71), and the inverse of the electrodonating power, Image ID:c1ob05856h-t4.gif (R2 = 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 (R2 = 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.

Graphical abstract: The nucleophilicity N index in organic chemistry

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Publication details

The article was received on 30 May 2011, accepted on 30 Jun 2011 and first published on 01 Jul 2011


Article type: Paper
DOI: 10.1039/C1OB05856H
Citation: Org. Biomol. Chem., 2011,9, 7168-7175
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    The nucleophilicity N index in organic chemistry

    L. R. Domingo and P. Pérez, Org. Biomol. Chem., 2011, 9, 7168
    DOI: 10.1039/C1OB05856H

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