Can four-membered heterophosphete structures exist? The contribution of phosphorus d orbitals to antiaromaticity

Zoltán Mucsi, Tamás Kötvélyesi, Béla Viskolcz, Imre G. Csizmadia, Tibor Novák, György Keglevich

Research output: Article

20 Citations (Scopus)

Abstract

The large instability of heterophosphete compounds, composed of a four-membered unsaturated ring with a pentavalent phosphorus atom and a heteroatom, has been identified and characterised by first-principle molecular orbital computations, at several levels of theory. It has been shown that strong electron-withdrawing groups bound to the phosphorus atom are able to stabilize the system. The extent of antiaromaticity of these compounds is examined and quantified by a linear aromatic and antiaromatic scale.

Original languageEnglish
Pages (from-to)1759-1767
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
Publication statusPublished - jún. 22 2007

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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