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Dependence of the long‐range phosphorus–hydrogen coupling constant nJP–H (n = 3,6,7) on the bond order between phosphorus and its substituents: preparation and spectroscopic characterization of several phosphoramidates

The examination of spectra of a selected series of phosphoramidates showed that, in addition to a double bond, whenever there are one or two partial multiple bonds in the molecule the long‐range coupling constant, such as 6JP–H, 7JP–H and 3JP–H, either disappears or at least reduces. In particular, the experimental data indicate the unexpected effect of a partial multiple bond between phosphorus and fluorine in 7JP–H and 3JP–H. The preparation of the compounds p‐CH3C6H4NHP(O)Cl2 (II), p‐CH3C6H4NHP(O)(Cl)OC6H4CH3‐p (XIV), m‐CH3C6H4NHP(O)(Cl)OC6H4CH3‐p (XV), m‐CH3C6H4NHP(O)(Cl)OC6H4CH3‐m (XVI) and the rigid molecule CH3C6H3(NH)2P(O)Cl (XVII) are described and they are characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. Copyright © 2001 John Wiley & Sons, Ltd.