Pyrido-annellated diazaphospholenes and phospholenium ions

Zoltán Benko, Sebastian Burck, Dietrich Gudat, Martin Nieger, L. Nyulászi, Nicholas Shore

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Pyrido-annulated 1,3,2-diazaphospholenium ions and P-bis(trimethylsilyl)amino substituted 1,3,2-diazaphospholenes were synthesised and characterised by spectroscopic methods and single-crystal X-ray diffraction studies. The distribution of bond distances provided evidence for π-electron delocalisation in the fused ring system. This hypothesis was confirmed by calculations of magnetic (NICS, nucleus independent chemical shift) and geometrical (Bird index, bond shortening index) aromaticity indexes which attest aromatic character of the five-membered rings in the cations that is lost upon introduction of a substituent at the phosphorus atom. Computation of isodesmic reaction energies suggest that the reclamation of aromatic stabilisation energies in the products facilitates reaction of P-amino-subsituted annulated diazaphospholenes under cleavage of the fused ring system.

Original languageEnglish
Pages (from-to)4937-4945
Number of pages9
JournalJournal of the Chemical Society. Dalton Transactions
Issue number36
DOIs
Publication statusPublished - Jul 28 2008

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Ions
Reclamation
Birds
Chemical shift
Reaction products
Phosphorus
Cations
Stabilization
Single crystals
X ray diffraction
Atoms
Electrons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Pyrido-annellated diazaphospholenes and phospholenium ions. / Benko, Zoltán; Burck, Sebastian; Gudat, Dietrich; Nieger, Martin; Nyulászi, L.; Shore, Nicholas.

In: Journal of the Chemical Society. Dalton Transactions, No. 36, 28.07.2008, p. 4937-4945.

Research output: Contribution to journalArticle

Benko, Zoltán ; Burck, Sebastian ; Gudat, Dietrich ; Nieger, Martin ; Nyulászi, L. ; Shore, Nicholas. / Pyrido-annellated diazaphospholenes and phospholenium ions. In: Journal of the Chemical Society. Dalton Transactions. 2008 ; No. 36. pp. 4937-4945.
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