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

作者：D'Auria Maurizio^*

来源：Letters in Organic Chemistry, 2016, 13(1): 33-43.

DOI：10.2174/157017861301151202101846

• Aromatic stabilization energy
• aromaticity
• DFT calculations
• experimental resonance energy
• functionals
• pi orbitals

Background: Recently, the author of the article proposed a new index for the estimation of the aromatic character. The aromaticity index D, D = [pi(1)+Sigma(n)(2)(pi(1)-pi(n))](0)/[pi(1)+Sigma(n)(2)(pi(1)-pi(n))] 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.

• 出版日期2016