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Acetic anhydride in a glass bottle. Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. [4] The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between ...
A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O)) 2 O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. [2] Thus, (CH 3 CO) 2 O is called acetic ...
Acetic anhydride performs an electrophilic attack on the critical catalytic residue, Lys115, of acetoacetate decarboxylase to inactivate the enzyme. [13] The rate of inactivation was assessed through the hydrolysis of the synthetic substrate 2,4-dinitrophenyl propionate to dinitrophenol by acetoacetate decarboxylase. In the presence of acetic ...
The electrophilic Br-Br molecule interacts with electron-rich alkene molecule to form a π-complex 1. Forming of a three-membered bromonium ion The alkene is working as an electron donor and bromine as an electrophile. The three-membered bromonium ion 2 consisted of two carbon atoms and a bromine atom forms with a release of Br −.
A major factor in determining the reactivity of acyl derivatives is leaving group ability, which is related to acidity. Weak bases are better leaving groups than strong bases; a species with a strong conjugate acid (e.g. hydrochloric acid) will be a better leaving group than a species with a weak conjugate acid (e.g. acetic acid).
Thionyl chloride can be used in place of acetic anhydride to trigger the elimination for forming the electrophilic intermediate and supplying chloride as the nucleophile to give an α-chloro-thioether: [6] Example of the Pummerer rearrangement using thionyl chloride. Other anhydrides and acyl halides can give similar products. Inorganic acids ...
An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid. In organic chemistry, organic acid anhydrides contain the functional group −C(=O)−O−C(=O)−. Organic acid anhydrides often form when one equivalent of water is removed from two equivalents of an organic acid in a dehydration reaction.
Other electrophilic aromatic substitution reactions can also be promoted with trifluoroacetic anhydride, including nitration, sulfonation and nitrosylation. [2] Similar to acetic anhydride, trifluoroacetic anhydride can be used as a dehydrating agent and as an activator for the Pummerer rearrangement. [4]