Thiocarbonate

Thiocarbonate describes a family of anions with the general chemical formula CS
3−x
O2−
x
(x = 0, 1, or 2). 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.[1]

Organic compounds containing divalent functional groups similar to these anions are also called thiocarbonates.

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

Important derivatives of dithiocarbonates are the xanthates (O-esters of dithiocarbonates), with the formula ROCS
2
. These salts are typically prepared by the reaction of sodium alkoxides with carbon disulfide.

Another group of dithiocarbonates have the formula (RS)2CO.[2] They are often derived by hydrolysis of the corresponding trithiocarbonates (RS)2CS. 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:[3]

CS2 + 2 NaSH → Na2CS3 + H2S

Dimethyl trithiocarbonate, (CH3S)2CS, is organic and co-valent, not ionic.

Perthiocarbonates

Addition of sulfur to trithiocarbonate gives the perthiocarbonate anion CS2−
4
, which contains one sulfur–sulfur bond.[4]

Perthiocarbonic acid (or tetrathioperoxycarbonic acid / disulfanylmethanedithioic acid / CAS#13074-70-9[5]) has never been synthesized in the pure form but only as a dark brown solution.[6]

gollark: https://www.youtube.com/watch?v=SSiRkpgwVKY (with an ESP8266 though).
gollark: I think I read that the ESP32's I²S hardware could do something vaguely PWM-like up to 80MHz.
gollark: I don't know *that* much. It just seems like it might require a lot of routing table entries on every node to work.
gollark: Based on skimming the disaster radio routing protocol bit, it doesn't really have any defenses against malicious devices fiddling with routing, and may scale poorly (not sure exactly how the routing tables work).
gollark: Not the hardwarey/RF stuff, more like how you can efficiently do routing (even in the face of possibly malicious devices connected) and whatnot.

References

  1. Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
  2. Perumalreddy Chandrasekaran, James P. Donahue (2009). "Synthesis of 4,5-Dimethyl-1,3-dithiol-2-one". Org. Synth. 86: 333. doi:10.15227/orgsyn.086.0333.CS1 maint: uses authors parameter (link)
  3. R. E. Strube (1959). "Trithiocarbodiglycolic Acid". Org. Synth. 39: 967. doi:10.15227/orgsyn.039.0077.(a procedure for synthesis of K2CS3
  4. Sodium tetrathiocarbonate from PubChem
  5. Tetrathioperoxycarbonic acid from PubChem
  6. A Text-book of Inorganic Chemistry, Volume 7, Issue 2, 1931, p. 269
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