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- Meldrums_acid abstract "Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid. The correct structure is shown on this page.As an alternative to its original preparation, Meldrum's acid can be synthesized from malonic acid, isopropenyl acetate, and catalytic sulfuric acid. Meldrum's acid has a high acidity with a pKa of 4.97. Meldrum's acid high acidity was long considered \"anomalous\" given it is 8 orders of magnitude more acidic than the highly related compound, dimethyl malonate (whose aqueous pKa is around 13). In 2004, Ohwada and coworkers resolved the Meldrum acid anomaly by performing several calculations. Ohwada noticed that the energy-minimizing conformation structure of the compound places the alpha proton's σCH orbital in the proper geometry to align with the π*CO, so that the ground state poses unusually strong destabilization of the C-H bond.Because of its great acidity, Meldrum's acid, like malonic acid, can serve as a reactant in Knoevenagel condensations.".
- Meldrums_acid iupacName "2,2-Dimethyl-1,3-dioxane-4,6-dione".
- Meldrums_acid thumbnail Meldrums_acid.png?width=300.
- Meldrums_acid wikiPageExternalLink s-2004-829539.pdf.
- Meldrums_acid wikiPageID "2529979".
- Meldrums_acid wikiPageLength "7790".
- Meldrums_acid wikiPageOutDegree "29".
- Meldrums_acid wikiPageRevisionID "693324816".
- Meldrums_acid wikiPageWikiLink Acetic_anhydride.
- Meldrums_acid wikiPageWikiLink Acetone.
- Meldrums_acid wikiPageWikiLink Acid.
- Meldrums_acid wikiPageWikiLink Acid_dissociation_constant.
- Meldrums_acid wikiPageWikiLink Acyl.
- Meldrums_acid wikiPageWikiLink Acyl_chloride.
- Meldrums_acid wikiPageWikiLink Andrew_Norman_Meldrum.
- Meldrums_acid wikiPageWikiLink Carbon_dioxide.
- Meldrums_acid wikiPageWikiLink Category:Dioxanes.
- Meldrums_acid wikiPageWikiLink Category:Lactones.
- Meldrums_acid wikiPageWikiLink Category:Organic_acids.
- Meldrums_acid wikiPageWikiLink Condensation_reaction.
- Meldrums_acid wikiPageWikiLink Deprotonation.
- Meldrums_acid wikiPageWikiLink Haloalkane.
- Meldrums_acid wikiPageWikiLink Ketene.
- Meldrums_acid wikiPageWikiLink Knoevenagel_condensation.
- Meldrums_acid wikiPageWikiLink Knorr_pyrrole_synthesis.
- Meldrums_acid wikiPageWikiLink Lactone.
- Meldrums_acid wikiPageWikiLink Malonic_acid.
- Meldrums_acid wikiPageWikiLink Malonic_ester_synthesis.
- Meldrums_acid wikiPageWikiLink Organic_compound.
- Meldrums_acid wikiPageWikiLink Pericyclic_reaction.
- Meldrums_acid wikiPageWikiLink Pyrolysis.
- Meldrums_acid wikiPageWikiLink Sulfuric_acid.
- Meldrums_acid wikiPageWikiLink Tert-Butyl_alcohol.
- Meldrums_acid wikiPageWikiLink File:Meldrum-alkylation.png.
- Meldrums_acid wikiPageWikiLink File:Meldrum-pyrolysis-nucleophile.png.
- Meldrums_acid wikiPageWikiLink File:Meldrums_acid_synthesis.png.
- Meldrums_acid wikiPageWikiLinkText "Meldrum's acid".
- Meldrums_acid imagefile "meldrum's_acid.png".
- Meldrums_acid imagename "Meldrum's Acid".
- Meldrums_acid iupacname "22".
- Meldrums_acid name "Meldrum's Acid".
- Meldrums_acid verifiedrevid "413090493".
- Meldrums_acid watchedfields "changed".
- Meldrums_acid wikiPageUsesTemplate Template:Chembox.
- Meldrums_acid wikiPageUsesTemplate Template:Chembox_Identifiers.
- Meldrums_acid wikiPageUsesTemplate Template:Chembox_Properties.
- Meldrums_acid wikiPageUsesTemplate Template:Chemspidercite.
- Meldrums_acid wikiPageUsesTemplate Template:Cite_journal.
- Meldrums_acid wikiPageUsesTemplate Template:Reflist.
- Meldrums_acid wikiPageUsesTemplate Template:Stdinchicite.
- Meldrums_acid subject Category:Dioxanes.
- Meldrums_acid subject Category:Lactones.
- Meldrums_acid subject Category:Organic_acids.
- Meldrums_acid hypernym Compound.
- Meldrums_acid type ChemicalCompound.
- Meldrums_acid type ChemicalSubstance.
- Meldrums_acid type Chemical.
- Meldrums_acid type Ester.
- Meldrums_acid type Ether.
- Meldrums_acid type Heterocycle.
- Meldrums_acid type Lactone.
- Meldrums_acid type ChemicalObject.
- Meldrums_acid type Thing.
- Meldrums_acid type Q11173.
- Meldrums_acid comment "Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid.".
- Meldrums_acid label "Meldrum's acid".
- Meldrums_acid sameAs Q421283.
- Meldrums_acid sameAs Meldrumsäure.
- Meldrums_acid sameAs اسید_ملدرام.
- Meldrums_acid sameAs Meldrumin_happo.
- Meldrums_acid sameAs Acide_de_Meldrum.
- Meldrums_acid sameAs Meldrum-sav.
- Meldrums_acid sameAs Acido_di_Meldrum.
- Meldrums_acid sameAs メルドラム酸.
- Meldrums_acid sameAs m.07l7nj.
- Meldrums_acid sameAs Meldrumska_kiselina.
- Meldrums_acid sameAs Meldrumska_kiselina.
- Meldrums_acid sameAs Мельдрумова_кислота.
- Meldrums_acid sameAs Q421283.
- Meldrums_acid sameAs 米氏酸.
- Meldrums_acid wasDerivedFrom Meldrums_acid?oldid=693324816.
- Meldrums_acid depiction Meldrums_acid.png.
- Meldrums_acid isPrimaryTopicOf Meldrums_acid.
- Meldrums_acid name "Meldrum's Acid".