Synthesis and characterization of N-thiophosphorylated thioureas RC(S)NHP(S)(OiPr)(2) (p-(4-imidazol-1-yl)-C6H4NH, p-N C-C6H4NH, (CH2=CH-CH2)(2)N): Unexpected formation of o-HO-C6H4NHC(S)NHP(S)(OiPr)(2) from p-N C-C6H4NHC(S)NHP(S)(OiPr)(2)

摘要

Reaction of p-(4-imidazol-1-yl)-C6H4NH2, P-N=C-C6H4NH2 or (CH2=CH-CH2)(2)NH with O,O'-diisopropylthiophosphoric acid isothiocyanate (iPrO)(2)P(S)NCS leads to p-(4-imidazoI-I-yI)-C(6)H(4)NHQS) NHP(S)(OiPr)(2) (W), p-N=C-C6H4NHC(S)NHP(S)(OiPr)(2) (HLII) and (CH2=CH-CH2)(2)NC(S)NHP(S)(OiPr)(2) Recrystallization of HLII from 96% aqueous EtOH solution leads to the formation of o-HO-C6H4NHC(S)NHP(S)(OiPr)(2) (HLIV).The structures of HLIV were investigated by H-1 and P-31(H-1) NMR spectroscopy, and microanalysis. The molecular structures of HLIV were elucidated by single crystal X-ray diffraction analysis. Single crystal X-ray diffraction studies showed that HLIV form both intra- and intermolecular hydrogen bonds, the latter leading to the formation of polymeric chains.