Abstract
Abstract In order to clarify the electron structure of carbonyl-stabilized phosphorus ylides, measurements of X-ray photoelectron spectroscopy (XPS) and combustion heat were performed. NMR and IR spectra were also measured as complementary methods. The results suggest that carbomethoxymethylenetriphenylphosphorane has a major contribution of polar bond (\overset+P—\overset−C) structure, whereas benzoylmethylenetriphenylphosphoranes have a larger contribution of covalent bond (P=C). A dπ–pπ interaction in the P–C bond was interpreted for XPS and NMR. The data for heat of combustion suggest that a large contribution of the polar bond structure brings about stabilization of the ylide molecule. These results show that XPS and combustion heat measurements are useful means for the analysis of ylide bonding.
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