Synthesis and characterization of N-phosphorylated thioureas RNHC(S)NHP(O)(OiPr)₂ (R = 2-MeC₆H₄, 2,6-Me₂C₆H₃, 2,4,6-Me₂C₆H₃)

Abstract

Reaction of O,O′-diisopropylphosphoric acid isothiocyanate (iPrO)₂P(O)NCS with 2-methylaniline 2-MeC₆H₄NH₂, 2,6-dimethylaniline 2,6-Me₂C₆H₃NH₂ or 2,4,6-trimethylaniline 2,4,6-Me₃C₆H₂NH₂ leads to the N-phosphorylated thioureas RNHC(S)NHP(O)(OiPr)₂ (R = 2-MeC₆H₄-, HL ^I; 2,6-Me₂C₆H₃-, HL ^II; 2,4,6-Me₃C₆H₂-, HL ^III). The new compounds were investigated by ¹H and ³¹P{¹H} NMR spectroscopy, and microanalysis. The molecular structure of the thiourea HL ^III was elucidated by single crystal X-ray diffraction analysis. Single crystal X-ray diffraction studies showed HL ^III forms both intra- and intermolecular hydrogen bonds, which in turn leads to the formation of polymeric chains. One of the intermolecular hydrogen bonds is of the type N-H…S. Moreover, the formation of intermolecular C-H…η ⁶-phenyl interactions was established.