Dihydroxydisulfane

Dihydroxydisulfane or hypodithionous acid is a reduced sulfur oxyacid with sulfur in a formal oxidation state of +1, but the valence of sulfur is 2. The structural formula is HO−S−S−OH, with all atoms arranged in a chain. It is an isomer of thiosulfurous acid but is lower in energy. Other isomers include HOS(=O)SH, HOS(=S)OH, and HS(=O)2SH. Disulfur monoxide, S2O, can be considered as the anhydride.[1] Unlike many of these other reduced sulfur acids, dihydroxydisulfane can be formed in a pure state by reacting hydrogen sulfide with sulfur dioxide at −70 °C in dichlorodifluoromethane.[2]

H2S + SO2 → H2S2O2
Dihydroxydisulfane
Names
Other names
Hydrogen disulfanediolate; Dihydroxidodisulfur; Disulfanediol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
164020
  • InChI=1S/H2O2S2/c1-3-4-2/h1-2H
    Key: JARODAOQOSWMRF-UHFFFAOYSA-N
  • OSSO
Properties
H2O2S2
Molar mass 98.13 g·mol−1
Conjugate base Disulfanediolate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dihyroxydisulfane may exist in an equilibrium with thiosulfurous acid.[3]

Organic derivatives such as dimethoxydisulfane,[4] diaceto disulfide,[5] and bis(trifluoroaceto) disulfide[6] also exist.

The conjugate bases are called disulfanediolate(1−) HSO−
2 and disulfanediolate(2−) SO2−
2.

Properties

Calculations predict that the S−S bond length is 2.013 Å, O−S bond length is 1.645 Å, H−O bond length is 0.943 Å.[7]

Related compounds include the isoelectronic substances hydrogen tetroxide HOOOOH, hydroxotrisulfane HOSSSH, HSOSSH, and tetrasulfane HSSSSH.

References
  1. Schmidt, Heinar; Steudel, Ralf; Suelzle, Detlev; Schwarz, Helmut (March 1992). "Sulfur compounds. 148. Generation and characterization of dihydroxy disulfide, HOSSOH: the chainlike isomer of thiosulfurous acid". Inorganic Chemistry. 31 (6): 941–944. doi:10.1021/ic00032a004.
  2. Makarov, Sergei V.; Makarova, Anna S.; Silaghi-Dumitrescu, Radu (2014). "Sulfoxylic and thiosulfurous acids and their dialkoxy derivatives". PATAI's Chemistry of Functional Groups. John Wiley & Sons. pp. 266–273. doi:10.1002/9780470682531.pat0829. ISBN 9780470682531.
  3. Patai, Saul (2015-04-20). The Chemistry of Peroxides. John Wiley & Sons. ISBN 9781118412718.
  4. Baumeister, Edgar; Oberhammer, Heinz; Schmidt, Heinar; Steudel, Ralf (December 1991). "Gas phase structure and vibrational spectra of dimethoxysulfane (CH3O)2S". Heteroatom Chemistry. 2 (6): 633–641. doi:10.1002/hc.520020605.
  5. Du, Lin; Yao, Li; Ge, Maofa (November 2007). "He I Photoelectron Spectroscopy and Theoretical Investigation on Diaceto Disulfide, CH3C(O)OSSOC(O)CH3". The Journal of Physical Chemistry A. 111 (46): 11787–11792. Bibcode:2007JPCA..11111787D. doi:10.1021/jp075164h. PMID 17958404.
  6. Zeng, Xiaoqing; Ge, Maofa; Sun, Zheng; Wang, Dianxun (May 2006). "Bis(trifluoroaceto) Disulfide (CF3C(O)OSSOC(O)CF3): A HeI Photoelectron Spectroscopy and Theoretical Study". The Journal of Physical Chemistry A. 110 (17): 5685–5691. Bibcode:2006JPCA..110.5685Z. doi:10.1021/jp061050e. PMID 16640363.
  7. Patai, Saul (2004). The Chemistry of Peroxides. Vol. 3 part 1. John Wiley & Sons. p. 296. ISBN 9781118412718.


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