S. Archer, T. Modro, L. Nassimbeni
Aug 1, 1981
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract The Crystal and molecular structure of benzyltriphenylphosphonium iodide was determined. This salt crystallises in space group P21/c, with a = 9.692(5), b = 21.58(1), c = 11.211(6) A; β = 107.2(2)°; Z = 4. The structure was refined to a final R value of 0.052. This structure, together with all structures of the quaternary phosphonium salts R4P+ X−, available through the CCDC file, was subject to the correlation treatment, introduced by Dunitz et al. Exclusive “face” orientation of X− with respect to the tetrahedral phosphonium center was demonstrated. Analysis of the secondary interactions of X− with the organic cation indicated that systems studied yield better models for ylid formation (α-hydrogen abstraction) than models for nucleophilic attack at the PIV atom.