Crystallographic evidence for the electronic distribution in (2,4-cyclopentadien-1-yl-idenehydrazono)triphenylphosphorane

Acta Crystallogr C. 1999 Jun 15:55 ( Pt 6):1016-9. doi: 10.1107/s0108270199002553.

Abstract

The title compound, C23H19N2P, can be graphically represented by several canonical forms. Its crystal structure analysis shows a clear bond alternation in the cyclopentadiene ring, which continues in the azo substructure, indicating that the resonance form containing the nonaromatic neutral cyclopentadienylidene moiety describes the actual hybrid form better than other 'inner ionic' resonance forms containing the aromatic anionic cyclopentadienylic portion. The preference for an s-transoid (E) geometry for the P1-N1-N2-C1 substructure was also confirmed over the other possible s-cisoid (Z) conformer.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Crystallography, X-Ray
  • Electrons
  • Hydrazones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Phosphoranes

Substances

  • (2,4-cyclopentadien-1-ylidenehydrazono)triphenylphosphorane
  • Hydrazones
  • Organophosphorus Compounds
  • Phosphoranes