Synthesis and characterization of N-thiophosphorylated thioureas RC(S)NHP(S)(O iPr) 2 ( p-(4-imidazol-1-yl)–C 6H 4NH, p-N [tbnd]C–C 6H 4NH, (CH 2[dbnd]CH–CH 2) 2N): Unexpected formation of o-HO–C 6H 4NHC(S)NHP(S)(O iPr) 2 from p-N [tbnd]C–C 6H 4NHC(S)NHP(S)(O iPr) 2

Abstract

Reaction of p-(4-imidazol-1-yl)–C 6H 4NH 2, p-N C–C 6H 4NH 2 or (CH 2 CH–CH 2) 2NH with O, O′-diisopropylthiophosphoric acid isothiocyanate ( iPrO) 2P(S)NCS leads to p-(4-imidazol-1-yl)–C 6H 4NHC(S)NHP(S)(O iPr) 2 ( HL I ), p-N C–C 6H 4NHC(S)NHP(S)(O iPr) 2 ( HL II ) and (CH 2 CH–CH 2) 2NC(S)NHP(S)(O iPr) 2 ( HL III ). Recrystallization of HL II from 96% aqueous EtOH solution leads to the formation of o-HO–C 6H 4NHC(S)NHP(S)(O iPr) 2 ( HL IV ). The structures of HL I–IV were investigated by 1H and 31P{ 1H} NMR spectroscopy, and microanalysis. The molecular structures of HL I,IV were elucidated by single crystal X-ray diffraction analysis. Single crystal X-ray diffraction studies showed that HL I,IV form both intra- and intermolecular hydrogen bonds, the latter leading to the formation of polymeric chains.