Mono-, di-, tri- and tetraphosphatriafulvenes: Electronic structure and aromaticity

Tibor Höltzl, Minh Tho Nguyen, T. Veszprémi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Aromaticity and electronic structure of triafulvenes containing 1, 2, 3 and 4 phosphorus atoms were studied using Density Functional Theory computations. It was found that the donor-acceptor interaction between the "filled" ring- and "empty" exo-Lewis-π orbitals is a good criterion for the aromaticity of triafulvenes. Although phosphorus is less electronegative than carbon, the exo-phosphorus increases, whereas the ring-phosphorus decreases the aromaticity. We have shown that the aromatic stabilization effect of the exo-phosphorus is larger than the destabilization of the ring-phosphorus. The final order of the aromaticity, compared with some reference compounds is cyclopropenone > 4-silatriafulvene ≈ 4-phosphatriafulvene > 1,4-diphosphatriafulvene > methylenecyclopropene > 1-phosphatriafulvene > 1,2,4-triphosphatriafulvene > 1,2-diphosphatriafulvene > 3,4-diphosphatriafulvene > 1,2,3,4-tetraphosphatriafulvene. The two last compounds are non-aromatic, ylidic structures.

Original languageEnglish
Pages (from-to)27-35
Number of pages9
JournalJournal of Molecular Structure: THEOCHEM
Volume811
Issue number1-3
DOIs
Publication statusPublished - Jun 1 2007

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Phosphorus
Electronic structure
phosphorus
electronic structure
rings
destabilization
Density functional theory
Carbon
Stabilization
stabilization
density functional theory
orbitals
Atoms
carbon
atoms
interactions

Keywords

  • Aromaticity
  • Density Functional Theory computations
  • Phosphatriafulvene
  • Three-membered ring
  • Triafulvenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Mono-, di-, tri- and tetraphosphatriafulvenes : Electronic structure and aromaticity. / Höltzl, Tibor; Nguyen, Minh Tho; Veszprémi, T.

In: Journal of Molecular Structure: THEOCHEM, Vol. 811, No. 1-3, 01.06.2007, p. 27-35.

Research output: Contribution to journalArticle

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