organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

, isothiouronium is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

with the formula SC(NH₂)₂sup>+ (R =

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...

) and is the

acid salt Acid salts are a class of salts that produce an acidic solution after being dissolved in a solvent. Its formation as a substance has a greater electrical conductivity than that of the pure solvent. An acidic solution formed by acid salt is made duri ...

of isothiourea. The H centres can also be replaced by alkyl and aryl. Structurally, these cations resemble

guanidinium Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experie ...

cations. The CN₂S core is planar and the C–N bonds are short.

Synthesis

Salts comprising these cations are typically prepared by

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

thiourea Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), except that the oxygen atom is replaced by a sulfur atom (as implied by the ''thio-'' prefix); however, the properties of urea ...

: :SC(NH₂)₂ + RX → SC(NH₂)₂sup>+X⁻

Reactions

Hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of isothiouronium salts gives

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

s. : SC(NH₂)₂sup>+X⁻ + NaOH → RSH + OC(NH₂)₂ + NaX Isothiouronium salts in which the sulfur has been alkylated, such as ''S''-methylisothiourea hemisulfate (CAS number: 867-44-7), will convert

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

s into

groups. This approach is sometimes called the Rathke synthesis after Bernhard Rathke who first reported it in 1881. : RNH₂ + eSC(NH₂)₂sup>+X⁻ → RNC(NH₂)₂]⁺X⁻ + MeSH Chelating resins with isothiouronium groups are used to recover mercury and other noble metals including platinum from solutions.{{cite web , url = http://www.purolite.com/default.aspx?RelID=606267&ProductID=19 , title = Purolite S920 Isothiouronium Chelating Resin , publisher = Purolite

References

Functional groups Thioureas Cations