Editing Enol (section)

== Stable enols ==
In general, enols are less stable than their keto equivalents because of the favorability of the C=O double bond over C=C double bond. However, enols can be stabilized kinetically or thermodynamically.{{cn|date=February 2024}}

Some enols are sufficiently stabilized kinetically so that they can be characterized.{{cn|date=February 2024}}
[[File:Hindrance.png|thumb|class=skin-invert-image|Diaryl-substitution stabilizes some enols.<ref>{{cite journal |title=Stable simple enols |journal=Journal of the American Chemical Society |year=1989 |doi=10.1021/ja00203a019}}</ref>]]

Delocalization can stabilize the enol tautomer. Thus, very stable enols are [[phenol]]s.<ref name=":0">{{Cite book|last=Clayden|first=Jonathan|title=Organic Chemistry|publisher=Oxford University Press|year=2012|pages=456–459}}</ref> Another stabilizing factor in 1,3-dicarbonyls is intramolecular hydrogen bonding.<ref>{{Cite journal|last1=Zhou|first1=Yu-Qiang|last2=Wang|first2=Nai-Xing|last3=Xing|first3=Yalan|last4=Wang|first4=Yan-Jing|last5=Hong|first5=Xiao-Wei|last6=Zhang|first6=Jia-Xiang|last7=Chen|first7=Dong-Dong|last8=Geng|first8=Jing-Bo|last9=Dang|first9=Yanfeng|last10=Wang|first10=Zhi-Xiang|date=2013-01-14|title=Stable acyclic aliphatic solid enols: synthesis, characterization, X-ray structure analysis and calculations|journal=Scientific Reports|language=en|volume=3|issue =1|pages=1058|doi=10.1038/srep01058|pmid=23320139|pmc=3544012|bibcode=2013NatSR...3E1058Z|issn=2045-2322|doi-access=free}}</ref> Both of these factors influence the enol-dione equilibrium in acetylacetone.