Literature DB >> 12633092

How aromatic are large (4n + 2)pi annulenes?

Chaitanya S Wannere1, Paul von Ragué Schleyer.   

Abstract

[structure: see text] While the total aromatic stabilization energies (ASE) of the [n]annulenes, from C(6)H(6) to C(66)H(66), converge to ca. 22 kcal/mol, the ASEs per pi-electron decrease markedly. Bond length alternation (which depends on the theoretical level) only reduces stabilization somewhat but influences the magnetic properties (NICS, proton chemical shifts, and magnetic susceptibilities) considerably. Nevertheless, these magnetic criteria, when based on the most realistic structures, agree that the aromaticities of the larger annulenes decrease and then nearly vanish.

Entities:  

Year:  2003        PMID: 12633092     DOI: 10.1021/ol027571b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

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3.  How do the Hückel and Baird Rules Fade away in Annulenes?

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  3 in total

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