Abstract
The thermodynamic data for the association of phenol with one phosphoryl stabilized and five carbonyl stabilized triphenylalkylidenephosphoranes in carbon disulphide solution have been determined. It was found that the phosphoranes due to charge delocalization, are very strong acceptors. The influence of various substituents in the phosphoranes on the hydrogen bond is discussed. The log K a55, − Δ H, v oo and the half band widths, v 1 2' , of the hydrogen bonded O-H band form linear relationships with Δ v OH. Also a linear relationship exists between the Taft σ * constant and −Δ H. Furthermore, a comparison of the NMB chemical shift, δ H', of the methylene C-H in the various phosphoranes with their rate constant with p-nitrobenzaldehyde, revealed an increasing rate constant with decreasing δ H value. A similar comparison between rate constant and Δ v OH showed some irregular trend.
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