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Thiocarbonate

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Thiocarbonate describes a family of anions with the general chemical formula CS
3−x
O2−
x
(x = 0, 1, or 2). Organic compounds structurally related to these anions are also called thiocarbonates.

Contents

Like the carbonate dianion, the thiocarbonates are planar, with carbon at the center. The average bond order from C to S or O is 1 13. The state of protonation is usually not specified. These anions are good nucleophiles and good ligands.

Monothiocarbonate

Monothiocarbonate is the dianion CO2S2−, which has C2v symmetry. Monothiocarbonate arises by the hydrolysis of thiophosgene or the reaction of base with carbonyl sulfide:

COS + 2 NaOH → Na2CO2S + H2O

Dithiocarbonates

Dithiocarbonate is the dianion COS2−
2
, which has C2v symmetry. It arises from the reaction of aqueous base with carbon disulfide:

CS2 + 2 NaOH → Na2COS2 + H2O

Probably the most important dithiocarbonates are the organic derivatives. The xanthates are organosulfur compounds prepared by the reaction of alkoxides with carbon disulfide. Charge-neutral organic dithiocarbonates, with the formula (RS)2CO, are also known, often being derived by hydrolysis of the corresponding organic trithiocarbonates. One example is tetrathiapentalenedione, a heterocycle that consists of two dithiocarbonate groups.

Trithiocarbonates

Trithiocarbonate is the dianion CS2−
3
, which has D3h symmetry. Trithiocarbonate is derived from the reaction of sulfide sources with carbon disulfide:

CS2 + 2 NaSH → Na2CS3 + H2S

Perthiocarbonates

Addition of sulfur to trithiocarbonate gives the perthiocarbonate anion CS2−
4
, which contains one sulfur–sulfur bond.
Perthiocarbonic acid (or tetrathiocarbonic acid, CAS#13074-70-9) has never been synthesized in the pure form but only as a dark brown solution.

References

Thiocarbonate Wikipedia


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