Thiopyrylium

Thiopyrylium
Names
	Preferred IUPAC name Thiopyrylium
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	9519339;
PubChem CID	11344401;
CompTox Dashboard (EPA)	DTXSID301028814 ;
	InChI InChI=1S/C5H5S/c1-2-4-6-5-3-1/h1-5H/q+1 Key: OKYDCMQQLGECPI-UHFFFAOYSA-N;
	SMILES [s+]1ccccc1;
Properties
Chemical formula	C5H5S+
Molar mass	97.16 g/mol
Solubility in water	Reacts
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Thiopyrylium is a cation with the chemical formula C₅H₅S⁺. It is analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom.

Thiopyrylium salts are less reactive than the analogous pyrylium salts due to the higher polarizability of the sulfur atom.^[2]^[3] Among the chalcogenic 6-membered unsaturated heterocycles, thiopyrylium is the most aromatic, due to sulfur having the similar Pauling electronegativity as carbon and only a slightly higher covalent radius.^[2] In water, thiopyrylium reacts to it and forms a mixture of 2-hydroxythiopyran and 4-hydroxythiopyran.^{[citation needed]}

Thiopyrylium salts can be synthesized by hydrogen abstraction from thiopyran by a hydride ion acceptor, such as trityl perchlorate.^[4]

The thiopyrylium analogue of 2,4,6-trisubstituted pyrylium salts can be synthesized by treatment with sodium sulfide followed by precipitation with acid. This reaction causes the oxygen atom in the pyrylium cation to be substituted with sulfur.^[3]

References

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1097. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b Tadeusz Marek Krygowski; Michal Ksawery Cyranski, eds. (2009). Aromaticity in Heterocyclic Compounds. Vol. 19 of Topics in Heterocyclic Chemistry. Springer. pp. 219–220. ISBN 9783540683292.
^ ^a ^b K. Dimroth; K. H. Wolf (2012). Wilhelm Foerst (ed.). Newer Methods of Preparative Organic Chemistry. Vol. 3. Elsevier. p. 361. ISBN 9780323146104.
^ "Thiopyrans". Concise Encyclopedia Chemistry. Walter de Gruyter. 1994. p. 1101. ISBN 9783110854039.

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[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1097. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[krygowski2009-2] Tadeusz Marek Krygowski; Michal Ksawery Cyranski, eds. (2009). Aromaticity in Heterocyclic Compounds. Vol. 19 of Topics in Heterocyclic Chemistry. Springer. pp. 219–220. ISBN 9783540683292.

[foerst2012-3] K. Dimroth; K. H. Wolf (2012). Wilhelm Foerst (ed.). Newer Methods of Preparative Organic Chemistry. Vol. 3. Elsevier. p. 361. ISBN 9780323146104.

[4] "Thiopyrans". Concise Encyclopedia Chemistry. Walter de Gruyter. 1994. p. 1101. ISBN 9783110854039.

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See also

References