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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/122/04/0549-0559

    • Keywords

       

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

    • Abstract

       

      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.

    • Author Affiliations

       

      Khodayar Gholivand1 Nasrin Oroujzadeh1 Zahra Shariatinia2

      1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
      2. Department of Chemistry, Amirkabir University of Technology, P. O. Box: 159163-4311, Tehran, Iran
    • Dates

       
  • Journal of Chemical Sciences | News

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