N-2,4-Dichlorobenzoyl phosphoric triamides: Synthesis, spectroscopic and X-ray crystallography studies

作者：Gholivand Khodayar^*; Oroujzadeh Nasrin; Shariatinia Zahra

来源：Journal of Chemical Sciences, 2010, 122(4): 549-559.

DOI：10.1007/s12039-010-0089-5

• Phosphoric triamides
• NMR
• long range coupling
• X-ray crystallography
• hydrogen bonds

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 (1)H, (13)C, (31)P NMR, IR spectroscopy and elemental analysis. Surprisingly, the (1)H NMR spectrum of 2 indicated long range (6)J (P, H) coupling constant = 1.3, 1.4 Hz and those of molecules 3, 4, 6-8 display long-range (4)J (H, H) coupling constants (1.8-1.9 Hz) for the coupling of aromatic protons in 2,4-dichlorophenyl rings. (1)H NMR spectra indicated (3)J (PNCH) for enantiotopic and diastereotopic benzylic CH(2) 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-Cl(2)-C(6)H(3)C(O)NHP(O)[NCH(2)CH(CH(3))(2)](2)) have been determined by X-raycrystallography. The structures form centrosymmetric dimers through intermolecular strong -P=O center dot center dot center dot H-N-hydrogen bonds. The dimers connect to each other via rather strong and weak C-H center dot center dot center dot O plus weak C-H center dot center dot center dot Cl H-bonds to produce a 1-D network for 5 while 3-D polymeric chains for 8 and 10.

• 出版日期2010-7