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Unprecedented acceleration of zirconium(IV)-assisted peptide hydrolysis at neutral pH

Miki Kassai1, R Gnana Ravi, Sarah J Shealy

  • 1Department of Chemistry, Center for Biotechnology and Drug Design, Georgia State University, P.O. Box 4098, Atlanta, Georgia 30302-4098, USA.

Inorganic Chemistry
|September 28, 2004
PubMed

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Acid Halides to Carboxylic Acids: Hydrolysis01:01

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...