Structure of the methoxide anion. Although alkali metal alkoxides are not salts and adopt complex structures, they behave chemically as sources of RO−.The structure of the methoxide ion.
In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as RO−, where R is the organyl substituent. Alkoxides are strong bases [citation needed] and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis.[1][2] Transition metal alkoxides are widely used for coatings and as catalysts.[3][4]
Enolates are unsaturated alkoxides derived by deprotonation of a C−H bond adjacent to a ketone or aldehyde. The nucleophilic center for simple alkoxides is located on the oxygen, whereas the nucleophilic site on enolates is delocalized onto both carbon and oxygen sites. Ynolates are also unsaturated alkoxides derived from acetylenic alcohols.
Phenoxides are close relatives of the alkoxides, in which the alkyl group is replaced by a phenyl group. Phenol is more acidic than a typical alcohol; thus, phenoxides are correspondingly less basic and less nucleophilic than alkoxides. They are, however, often easier to handle, and yield derivatives that are more crystalline than those of the alkoxides.
^Williamson, Alexander (1850). "Theory of Ætherification". Phil. Mag.37 (251): 350–356. doi:10.1080/14786445008646627. (Link to excerpt.)
^Boyd, Robert Neilson; Morrison, Robert Thornton (1992). Organic Chemistry (6th ed.). Englewood Cliffs, N.J.: Prentice Hall. pp. 241–242. ISBN 9780136436690.
^Bradley, Don C.; Mehrotra, Ram C.; Rothwell, Ian P.; Singh, A. (2001). Alkoxo and Aryloxo Derivatives of Metals. San Diego: Academic Press. ISBN 978-0-08-048832-5.
^Turova, Nataliya Y.; Turevskaya, Evgeniya P.; Kessler, Vadim G.; Yanovskaya, Maria I. (2002). The Chemistry of Metal Alkoxides. Dordrecht: Kluwer Academic Publishers. ISBN 9780792375210.
In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They...
Silicon alkoxides are a group of alkoxides, chemical compounds of silicon and an alcohol, with the formula Si(OR)4. Silicon alkoxides are important precursors...
A transition metal alkoxide complex is a kind of coordination complex containing one or more alkoxide ligands, written as RO−, where R is the organic substituent...
deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ion with a primary...
produced from epoxides. Nucleophilic displacement of alkyl halides by alkoxides R–ONa + R′–X → R–O–R′ + NaX This reaction, the Williamson ether synthesis...
conjugate sodium alkoxide base of the alcohol formed (e.g. sodium ethoxide if ethanol is formed) is often used, since the alkoxide is regenerated. In...
structure is more complex than suggested by its empirical formula. Like other alkoxides of titanium(IV) and zirconium(IV), it finds used in organic synthesis...
attack another carbonyl. In the final step of the reaction, the acid and alkoxide ions formed exchange a proton. In the presence of a very high concentration...
an anhydrous base to give an ester. Catalysts are aluminium alkoxides or sodium alkoxides. Benzaldehyde reacts with sodium benzyloxide (generated from...
the alkoxide generates a carboxylic acid: The alkoxide ion is a strong base so the proton is transferred from the carboxylic acid to the alkoxide ion...
tetrahedral intermediate, which then expels an alkoxide ion. The resulting carboxylic acid quickly protonates the alkoxide ion to give a carboxylate ion and an...
charged hydrogen ion (proton), much more readily than alcohols do (into an alkoxide ion and a proton), because the carboxylate ion is stabilized by resonance...
or TTIP, is a chemical compound with the formula Ti{OCH(CH3)2}4. This alkoxide of titanium(IV) is used in organic synthesis and materials science. It...
bonded to H it is an alcohol. An alkoxide can refer to salts of alcohols, and they are ionic compounds containing an alkoxide ions RO−; it is a derivative...
Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed...
malonate and the alcohol, while other alkoxide salts will cause scrambling by transesterification. Only the "same" alkoxide anion as the one that one used to...
alcohol/alkoxide solvating mixture must match the alkoxy components of the reacting esters to minimize the number of different products. Many alkoxides are...
NH4Cl → 1/n (NPCl2)n + 4 HCl When the chloride groups are replaced by alkoxide (RO−), a family of polymers is produced with potentially useful properties...
benzilic acid rearrangement, except that an alkoxide or an amide anion is used in place of a hydroxide ion. The alkoxide used should not be easily oxidizable...
to give, after aqueous workup, a tertiary alcohol With an alcohols or alkoxides to gives the hemiketal or its conjugate base. With a diol to the ketal...
example, when a 3° haloalkane is reacts with an alkoxide, due to strong basic character of the alkoxide and unreactivity of 3° group towards SN2, only...
neutral or positively charged. Examples of nucleophiles are hydroxide ion, alkoxides, amines and halides. This type of reaction is found mainly in aliphatic...
(C6H5–OH), which is acidic at the hydroxyl (OH), as charge on the oxygen (alkoxide –O−) is partially delocalized into the benzene ring. Although benzylic...
monomer. Nucleophilic initiators include covalent or ionic metal amides, alkoxides, hydroxides, cyanides, phosphines, amines and organometallic compounds...
presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective...
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