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Carbamylphosphonates and Related CompoundsNuclear-Magnetic-Resonance and Infrared Spectra

Volume 21, Number 1 (Feb. 1967) Page 9-15

Siddall, T.H.; Prohaska, C.A.

Proton magnetic resonance and infrared spectra were obtained for 44 carbamylphosphonates and related compounds, the common structural features being the grouping [Equation]

As with ordinary amides, slow rotation is observed around the carbonyl-to-nitrogen bond, but the chemical shift between nitrogen substituents is three to five times as great. Evidence is presented for long range coupling of phosphorus to protons in N-substituents. Correlations are observed between the carbonyl and phosphoryl stretching frequencies and substituents both on nitrogen and on phosphorus.