Substituent effects on the aromaticity of carbocyclic five-membered rings

Physical Chemistry Chemical Physics : PCCP
Mercedes Alonso, Bernardo Herradón

Abstract

The influence of the substituent nature, as well as the number and position of the substituents, on the aromaticity/antiaromaticity of a comprehensive set of derivatives of cyclopentadienyl anion, cyclopentadiene and cyclopentadienyl cation has been analyzed. The aromaticity/antiaromaticity of substituted cyclopentadienyl derivatives has been measured using energetic, magnetic and structural criteria to take into account the multidimensional character of aromaticity. Furthermore, the Euclidean distance values (d(j)) for all compounds have been estimated using the neural network developed previously. It has been demonstrated that the d(j) as a scale of aromaticity overcomes the particular limitations of the ASE, Lambda, NICS and HOMA indices to describe the changes in the aromaticity of cyclopentadiene ring due to substituent effects. Additionally, it is shown that neural networks are useful tools for establishing structure-property relationships. The results indicate that mostly the aromaticity of cyclopentadiene ring and cyclopentadienyl anion ring decrease upon substitution irrespective of the electronic character of the substituent. The electron-donating groups, especially hydroxyl groups, destabilize carbanion to a larger e...Continue Reading

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Citations

May 2, 2014·Chemical Reviews·Tadeusz M KrygowskiMarcin Palusiak
Aug 17, 2012·Journal of Molecular Modeling·Herbert C GeorgThaciana Malaspina
Sep 28, 2013·Journal of Molecular Modeling·Yingtao LiuWeiliang Zhu
Sep 1, 2011·Physical Chemistry Chemical Physics : PCCP·Mercedes AlonsoBernardo Herradón
Jan 31, 2012·Physical Chemistry Chemical Physics : PCCP·Rachael E H MilesJonathan P Reid
Feb 13, 2013·Physical Chemistry Chemical Physics : PCCP·Remi Chauvin, Christine Lepetit
Feb 24, 2016·Physical Chemistry Chemical Physics : PCCP·John C CancillaJosé S Torrecilla
Dec 21, 2012·Chemistry : a European Journal·Mercedes AlonsoFrank De Proft
Jul 19, 2012·Chemistry : a European Journal·Mercedes AlonsoFrank de Proft
May 13, 2015·Physical Chemistry Chemical Physics : PCCP·Debojit BhattacharyaDouglas J Klein
Mar 7, 2014·Physical Chemistry Chemical Physics : PCCP·M AlonsoF De Proft
Apr 14, 2016·The Journal of Physical Chemistry. a·Sarvesh Kumar PandeyHenry F Schaefer
Mar 1, 2016·Physical Chemistry Chemical Physics : PCCP·T WollerM Alonso
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Oct 12, 2010·The Journal of Physical Chemistry. a·Kevin W CormierMichael Lewis
Aug 23, 2017·Journal of the American Chemical Society·Paolo CostaWolfram Sander

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