Isothiouronium

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

  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.
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