Mosher's acid
Encyclopedia
Mosher's acid, or α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) is a carboxylic acid
which was first used by Harry Stone Mosher
as a chiral derivatizing agent. It is a chiral molecule, consisting of R and S enantiomers.
or amine
of unknown stereochemistry
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.
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...
which was first used by Harry Stone Mosher
Harry Stone Mosher
Harry Stone Mosher was an American chemist and the discoverer of Mosher's acid .-References:...
as a chiral derivatizing agent. It is a chiral molecule, consisting of R and S enantiomers.
Applications
As a chiral derivatizing agent, it reacts with an alcoholAlcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
or amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
of unknown stereochemistry
Stereochemistry
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules....
to form an ester or amide. The absolute configuration
Absolute configuration
An absolute configuration in stereochemistry is the spatial arrangement of the atoms of a chiral molecular entity and its stereochemical description e.g. R or S....
of the ester or amide is then determined by proton and/or 19F NMR spectroscopy
NMR spectroscopy
Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is a research technique that exploits the magnetic properties of certain atomic nuclei to determine physical and chemical properties of atoms or the molecules in which they are contained...
.
Mosher's acid chloride, the acid chloride form, is sometimes used because it has better reactivity.