# Thioenol

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{{short description|1=Organic compounds with the general structure C=C–SH}}
thumb|right|General chemical structure of a thioenol

In [organic chemistry](/source/organic_chemistry), '''thioenols''' (also known as '''alkenethiols''') are [alkene](/source/alkene)s with a [thiol group](/source/thiol_group) ({{chem2|\sSH}}) affixed to one of the [carbon](/source/carbon) atoms composing the [double bond](/source/double_bond) (i.e. {{chem2|C\dC\sSH}}). They are the [sulfur](/source/sulfur) analogs of [enol](/source/enol)s (hence the ''[thio-](/source/thio-)'' prefix). Alkenes with a thiol group on both atoms of the double bond are called '''enedithiols'''. [Deprotonated](/source/Deprotonation) anions of thioenols are called '''thioenolates'''. 

These structures exhibit [tautomerism](/source/tautomerism) to give [thioketone](/source/thioketone)s or [thioaldehyde](/source/thioaldehyde)s, analogous to  [keto–enol tautomerism](/source/keto%E2%80%93enol_tautomerism) of [carbonyl](/source/carbonyl) structures.<ref>{{cite journal |title= The acid dissociation constant of triphenylethenethiol, a simple thioenol, and that of its oxygen–enol analog |first1= Yvonne |last1= Chiang |first2= A. Jerry |last2= Kresge |first3= Norman P. |last3= Schepp |first4= Vladimir V. |last4= Popik |first5= Zvi |last5= Rappoport |first6= Tzvia |last6= Selzer |journal=  Canadian Journal of Chemistry |year= 1998 |volume= 76 |issue= 6 |pages= 657–661 |doi= 10.1139/v98-027 |doi-access= free }}</ref>

==References==
{{reflist}}

Category:Thiols
Category:Enols

{{organic-chem-stub}}

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Adapted from the Wikipedia article [Thioenol](https://en.wikipedia.org/wiki/Thioenol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Thioenol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.