Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 1 (January 2007)

organic compounds

 

Cyano-stabilized triphenylphosphonium ylids

F. Castañeda, C. A. Bunton, R. Baggio and M. T. Garland

Abstract: Crystalline cyano-stabilized triphenylphosphonium ylids with keto or ester groups give rise to an extended electronic delocalization. In methyl 2-cyano-2-(trimethylphosphonio)ethenoate, Ph₃P=C(CN)CO₂CH₃ or C₂₂H₁₈NO₂P, (I), and 1-cyano-1-(trimethylphosphonio)prop-1-en-2-olate, Ph₃P=C(CN)CO-CH₃ or C₂₂H₁₈NOP, (II), the carbonyl groups are oriented toward the cationoid P atom. Bond lengths and angles, torsion angles and PO contact distances are consistent with a dominant coplanar conformation where the molecular structures are the result of a balance between intra- and intermolecular interactions. The main interactions presented by cyano-ester (I) and cyano-keto (II) are intramolecular interactions between the carbonyl O and the P atoms. In addition, both compounds show other less important intramolecular interactions between the carbonyl O and phenyl H atoms, which could contribute to form a preferred conformation in the crystal structure.

Formula: C₂₂H₁₈NO₂P and C₂₂H₁₈NOP

	Structure factor file (CIF format) (204.6 kbytes) [ doi:10.1107/S0108270106051201/sq3045Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (201.2 kbytes) [ doi:10.1107/S0108270106051201/sq3045IIsup3.hkl ] Contains datablock II

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