Isothiouronium

From Wikipedia, the free encyclopedia
Jump to: navigation, search

In organic chemistry, isothiouronium is a functional group with the formula [RSC(NH2)2]+ (R = alkyl, aryl). The H centres can also be replaced by alkyl and aryl. Structurally, these cations resemble guanidinium cations. The CN2S core is planar and the C-N bonds are short.[1]

Salts comprising these anions are typically prepared by alkylation of thiourea:

SC(NH2)2 + RX → [RSC(NH2)2]+X

Hydrolysis of isothiouronium salts gives thiols.[2]

[RSC(NH2)2]+X + NaOH → RSH + OC(NH2)2 + NaX

Chelating resins with isothiouronium groups are used to recover mercury and noble metals including platinum from solutions.[3]

References[edit]

  1. ^ Barker, J.; Powell, H. R. (1998). "S-Benzylisothiouronium Chloride". Acta Crystallographica Section C Crystal Structure Communications 54 (12): 2019. doi:10.1107/S0108270198008166. 
  2. ^ Helmer Kofod (1963). "Furfuryl Mercaptan". Org. Synth. 4: 13. ; Coll. Vol. 1, p. 66 
  3. ^ "Purolite S920 Isothiouronium Chelating Resin". Purolite.