Synthesis and spectroscopic study of some new phosphoramidates, crystal structures of N-benzoyl-N′,N′′-bis(azetidinyl)phosphoric triamide and N-benzoyl-N′,N"-bis(hexamethylenyl)phosphoric triamide

Some new N-carbonyl, phosphoramidates with formula C6H5C(O)N(H)P(O)R-2 (R = NC3H6 (1), NC6H12 (2), NHCH2CH = CH2 (3), N(C3H7)(2) (4)) and CCl3C(O)N(H)P(O)R'(2) (R' = NC3H6 (5), NHCH2CH = CH2 (6)) were synthesized and characterized by H-1, C-13, P-31 NMR and IR spectroscopy and elemental analysis. The structures were determined for compounds 1 and 2. Compound I exists as two crystallographically independent molecules in crystal lattice. Both compounds I and 2 produced dimeric aggregates via intermolecular -P=O...H-N- hydrogen bonds, which in compound 2 is a centrosymmetric dimer. In compounds with four-membered ring amine groups, (3)J(P,C)>(2)J(P,C), in agreement with our previous studies about five-membered ring amine groups. Also, (3)J(P,.C) values in compounds 1 and 5 are greater than in compounds with five-, six- and seven-membered ring amine groups.