Double group transfer reactions as indicators of aromatic stabilization

Gernot Frenking, Fernando P. Cossío, Miguel A. Sierra, Israel Fernández

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

The main features of double hydrogen atom transfer reactions in syn-sesquinorbornanes, which involve the concomitant formation of an aromatic ring, have been studied computationally within the framework of Density Functional Theory. The very good linear correlations, which exhibit high correlation coefficients between the recently available Aromatic Stabilization Energies (ASE) from the Energy Decomposition Analysis (EDA) method and the activation and reaction energies, as well as geometric features (C-C bond lengths) of the corresponding transition states of the transformations, suggest that the calculated values are useful in estimating the aromatic character of a molecule. The studied process may be used for benchmarking of energetic aromatic indices.

Original languageEnglish
Pages (from-to)5410-5415
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number32
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • Aromatic stabilization energy
  • Aromaticity
  • Density functional calculations
  • Double group transfer reactions

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