Syntheses and spectroscopic study of some new N-4-fluorobenzoyl phosphoric triamides;: crystal structures of 4-F-C6H4C(O)N(H)P(O)R2, R = NHC(CH3)3, NH-CH2C6H5, N(CH3CH2C6H5)

Some new N-4-Fluorobenzoyl phosphoric triamides with formula 4-F-C6H4C(O)N(H)P(O)X-2, X = NH-C(CH3)(3) (1), NH-CH2-CH=CH2 (2), NH-CH2C6H5 (3), N(CH3)(C6H5) (4), NHCH(CH3)(C6H5) (5) were synthesized and characterized by H-1, C-13, P-31 NMR, IR and Mass spectroscopy and elemental analysis. The structures of compounds 1, 3 and 4 were investigated by X-ray crystallography. The P = 0 and C = 0 bonds in these compounds are anti. Compounds I and 3 form one dimensional polymeric chain produced by intra- and intermolecular -P=(OH)-H-...-N- hydrogen bonds. Compound 4 forms only a centrosymmetric dimer in the crystalline lattice via two equal -P=(OH)-H-...-N- hydrogen bonds. H-1 and C-13 NMR spectra show two series of signals for the two amine groups in compound 1. This is also observed for the two alpha-methylbenzylamine groups in 5 due to the presence of chiral carbon atom in molecule. C-13 NMR spectrum of compound 4 shows that (2)J(P,C-aliphatic) coupling constant for CH2 group is greater than for CH3 in agreement with our previous study Mass spectra of compounds 1-3 (containing 4-F-C6H4C(O)N(H)P(O) moiety) indicate the fragments of amidophosphoric acid and 4-F-C6H4CN+ that formed in a pseudo McLafferty rearrangement pathway. Also, the fragments of aliphatic amines have high intensity in mass spectra.