Crystallographic evidence for the electronic distribution in (2,4-cyclopentadien-1-yl-idenehydrazono)triphenylphosphorane.
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.
Department of Chemistry, University of Illinois, Urbana 61801, USA.
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Minutolo
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Wilson
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Katzenellenbogen
D018360:Crystallography, X-Ray; D004583:Electrons; D006835:Hydrazones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010753:Phosphoranes
C120469:(2,4-cyclopentadien-1-ylidenehydrazono)triphenylphosphorane; D006835:Hydrazones; D009943:Organophosphorus Compounds; D010753:Phosphoranes