A New Index for the Estimation of the Aromatic Character - IX

Author(s): Maurizio D`Auria*.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 1 , 2016

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Abstract:

Background: Recently, the author of the article proposed a new index for the estimation of the aromatic character. The aromaticity index D, D usually obtained by using DFT/B3LYP/6-311G+(d,p) theoretical method.

Method: The D index was tested using different functionals: LSDA, BVP86, B3LYP, CAM-B3LYP, B3PW91, mPW1PW91, PBEPBE, HSE1PBE, HCTH, TPSSTPSS, and wB97XD.

Results: The results showed that the D values for monocyclic aromatic compounds are not largely sensible to the variation of the functional. Large variations of D values were observed for polycyclic aromatic compounds. D values were correlated to ERE (experimental resonance energy) and ASE (aromatic stabilization energy). ERE and ASE gave different correlations with D.

Conclusion: The best correlation between D and ERE was obtained by using CAM-B3LYP. The best correlation between D and ASE was obtained by using CAM-B3LYP.

Keywords: Aromatic stabilization energy, aromaticity, DFT calculations, experimental resonance energy, functionals, π orbitals.

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Article Details

VOLUME: 13
ISSUE: 1
Year: 2016
Page: [33 - 43]
Pages: 11
DOI: 10.2174/157017861301151202101846

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