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Issue 18, 2015
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Quantifying aromaticity with electron delocalisation measures

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Abstract

Aromaticity cannot be measured directly by any physical or chemical experiment because it is not a well-defined magnitude. Its quantification is done indirectly from the measure of different properties that are usually found in aromatic compounds such as bond length equalisation, energetic stabilisation, and particular magnetic behaviour associated with induced ring currents. These properties have been used to set up the myriad of structural-, energetic-, and magnetic-based indices of aromaticity known to date. The cyclic delocalisation of mobile electrons in two or three dimensions is probably one of the key aspects that characterise aromatic compounds. However, it has not been until the last decade that electron delocalisation measures have been widely employed to quantify aromaticity. Some of these new indicators of aromaticity such as the PDI, FLU, ING, and INB were defined in our group. In this paper, we review the different existing descriptors of aromaticity that are based on electron delocalisation properties, we compare their performance with indices based on other properties, and we summarise a number of applications of electronic-based indices for the analysis of aromaticity in interesting chemical problems.

Graphical abstract: Quantifying aromaticity with electron delocalisation measures

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Publication details

The article was received on 02 Feb 2015 and first published on 10 Apr 2015


Article type: Review Article
DOI: 10.1039/C5CS00066A
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Citation: Chem. Soc. Rev., 2015,44, 6434-6451
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    Quantifying aromaticity with electron delocalisation measures

    F. Feixas, E. Matito, J. Poater and M. Solà, Chem. Soc. Rev., 2015, 44, 6434
    DOI: 10.1039/C5CS00066A

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