On the aromatic stabilization energy of the 4N π electron pyrene

Abstract

The aromatic stabilization energy (ASE) of pyrene, evaluated with both isodesmic equation and ab initio valence bond (VB) theory-based block localized wavefunction (BLW) methods, gives consistent results (ca 74 kcal/mol). Biphenyl, phenanthrene and benzene, evaluated similarly, all have essentially the same ASEs per ring carbon. The aromaticity of pyrene is not diminished because of its 4n π electron count.

Keywords:

• pyrene
• aromatic stabilization energy
• Pauling–Wheland resonance energy
• extra cyclic resonance energy
• block-localized wavefunction

Acknowledgements

We dedicate this paper to Professor H. F. Schaefer on the occasion of his 65th birthday. We gratefully acknowledge financial support from Grant 120000-501/68-BW-172104 (M. K. C.), from the Natural Sciences and Engineering Research Council for Canada (NSERC) (G. J. B.), and from National Science Foundation Grant CHE-0716718 (P. v. R. S.). The Interdisciplinary Centre for Mathematical and Computational Modeling (Warsaw, Poland) provided computational facilities.