Thiocyanate functionalised ionic liquids: synthesis, characterisation and reactivity

The reaction of chloromethyl thiocyanate with 1-methylimidazole affords the imidazolium salt, 1-thiocyanomethyl-3-methylimidazolium chloride, [C<SUB >1</SUB >SCNmim]Cl (<B >1a</B >). Exchange of the chloride anion in <B >1a</B > by [PF<SUB >6</SUB >]<SUP >-</SUP >, [BF<SUB >4</SUB >]<SUP >-</SUP >, [Tf<SUB >2</SUB >N]<SUP >-</SUP > or [AuCl<SUB >4</SUB >]<SUP >-</SUP > affords salts <B >1b</B >, <B >1c</B >, <B >1d</B > and <B >1e</B >, respectively. Salts [C<SUB >1</SUB >SCNmim][BF<SUB >4</SUB >] (<B >1c</B >) and [C<SUB >1</SUB >SCNmim][Tf<SUB >2</SUB >N] (<B >1d</B >) melt below 100 °C and can therefore be classified as ionic liquids. The reaction of <B >1a</B > with PdCl<SUB >2</SUB > affords [C<SUB >1</SUB >SCNmim]<SUB >2</SUB >[PdCl<SUB >4</SUB >] (<B >2a</B >), whereas <B >1c</B > reacts with PdCl<SUB >2</SUB > to form the complex [PdCl<SUB >2</SUB >{C<SUB >1</SUB >SCNmim}<SUB >2</SUB >][BF<SUB >4</SUB >]<SUB >2</SUB > (<B >2c</B >). In the presence of HNO<SUB >3</SUB > both <B >1a</B > and <B >1c</B > react with PdCl<SUB >2</SUB > with the loss of HCN to form a sulfide-bridged palladium dimer [PdCl<SUB >2</SUB >{C<SUB >1</SUB >Smim}]<SUB >2</SUB > (<B >3</B >). The structures of <B >1a</B >, <B >1e</B >, <B >2a</B > and <B >3</B > have been determined in the solid state by single-crystal X-ray diffraction.


Published in:
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2, 279 – 284
Year:
2007
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 Record created 2007-01-17, last modified 2018-03-17


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