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Abstract
The structure and absolute configuration of enantiomeric (SP)-L-menthyl (2-methoxy-phenyl)phenylphosphinylacetate, the only crystalline of the two P-epimers, was analyzed by a singlecrystal X-ray diffraction technique. C25H33O4P, space group P212121, a = 9.890(1)Å, b = 10.011(3)Å, c = 24.177(3)Å, V = 2393.7(8)Å3, Z = 4. The structure was solved by direct methods and was refined by full matrix least-squares calculations to R = 0.045 using 2697 unique reflections with I > 3σ(I). The absolute configuration was determined by the Hamilton method. The P˭O and C˭O dipoles of the studied molecule were found oriented in a syn fashion and the phenyl and the methoxyphenyl rings were both arranged coplanarly with the P˭O bond. Two intermolecular C‒H…O short contacts involving methoxyphenyl hydrogens and P˭O and C˭O oxygens were revealed. A potential possibility of using differentiated crystallinity of P-epimeric menthyl phosphinylacetates as a mnemonic for the assignment of their configuration at P is discussed.