Mosher's acid, or α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) is a

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

which was first used by

Harry Stone Mosher Harry Stone Mosher (August 31, 1915 – March 2, 2001) was an American chemist and the discoverer of Mosher's acid. Early life Mosher attended Willamette University in Salem, Oregon, where he received a bachelor's degree in chemistry in 1937. ...

as a

chiral derivatizing agent A chiral derivatizing agent (CDA) also known as a chiral resolving reagent, is a chiral auxiliary used to convert a mixture of enantiomers into diastereomers in order to analyze the quantities of each enantiomer present within the mix. Analysis can ...

. It is a chiral molecule, consisting of ''R'' and ''S'' enantiomers.

Applications

As a chiral derivatizing agent, it reacts with an

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

or amine of unknown

stereochemistry Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereois ...

to form an ester or amide. The absolute configuration of the ester or amide is then determined by proton and/or ¹⁹F NMR spectroscopy. Mosher's acid chloride, the acid chloride form, is sometimes used because it has better reactivity.

References

{{Reflist Stereochemistry Carboxylic acids Trifluoromethyl compounds Phenyl compounds

Applications

See also

References