New phosphoric triamides 1-9 were synthesized by the reaction of 𝑁-2,4-dichlorobenzoyl phosphoramidic dichloride with various cyclic aliphatic amines and the products were characterized by ¹H, ¹³C, ³¹P NMR, IR spectroscopy and elemental analysis. Surprisingly, the ¹H NMR spectrum of 2 indicated long range ${}^6J$ (P, H) coupling constant = 1.3, 1.4 Hz and those of molecules 3, 4, 6-8 display longrange ${}^4J$ (H, H) coupling constants ($1.8-1.9$ Hz) for the coupling of aromatic protons in 2,4-dichlorophenyl rings. ¹H NMR spectra indicated ${}^3J$ (PNCH) for enantiotopic and diastereotopic benzylic CH₂ protons in compounds 7 and 8. The spectroscopic data of newly synthesized compounds were compared with those related 𝑁-benzoyl derivatives. The structures of compounds 5, 8 and 10 (2,4-Cl₂-C₆H₃C(O)NHP(O)[NCH₂CH(CH₃)₂]₂) have been determined by X-ray crystallography. The structures form centrosymmetric dimers through intermolecular strong -P=O…H-N-hydrogen bonds. The dimers connect to each other via rather strong and weak C-H…O plus weak C-H…Cl H-bonds to produce a 1-D network for 5 while 3-D polymeric chains for 8 and 10.

The reaction of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson reagent) with isobutanol, cyclohexylamine and phenylethylamine produced (4-methoxy-phenyl)-phosphonodithioic acid o-isobutyl ester HS₂P(p-C₆H₄OMe) (OCH₂CH(CH₃)₂) (I), [S₂P(C₆H₁₁NH)(p-C₆H₄OMe) H₃N⁺C₆H₁₁] (II) and [S₂P(phCH₂CH₂NH) (p-C₆H₄OMe)H₃N⁺CH₂CH₂ph] (III), respectively. The reaction of alcohol with Lawesson reagent produced neutral product (I) while that with amines led to an ion pair (II, III). Furthermore, reaction of I, II and III with NiCl₂.6H₂O in methanol produced novel complexes: IV, V and VI. The compounds were characterized by ¹H, ¹³C and ³¹P NMR, IR spectroscopy and elemental analysis. The single crystal X-ray structures of IV and V showed that the nickel complexes are square planar. Compound V formed a three-dimensional supramolecular structure via intermolecular P-O…H-N hydrogen bonds. The Xray crystallography of V showed that those three hydrogens of ⁺NH₃ cation produced three hydrogen bonds with different distances. The new compounds were additionally tested in view of their anti-bacterial properties. The ligands containing amine substituents exhibited more activity toward tested bacteria than their alcohol substituents, while the Ni(II) complexes including alcohol substituents exhibited high potential.