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That is, on reflecting the meso compound through a mirror plane perpendicular to the screen, the same stereochemistry is obtained; this is not the case for the non-meso tartaric acid, [3] which generates the other enantiomer. The meso compound must not be confused with a 50:50 racemic mixture of the two optically-active compounds, although ...
However, compounds that contain an even number of asymmetric atoms sometimes lack chirality because they are arranged in mirror-symmetric pairs, and are known as meso compounds. For instance, meso tartaric acid (shown on the right) has two asymmetric carbon atoms, but it does not exhibit enantiomerism because there is a mirror symmetry plane.
Pure enantiomers also exhibit the phenomenon of optical activity and can be separated only with the use of a chiral agent. In nature, only one enantiomer of most chiral biological compounds, such as amino acids (except glycine, which is achiral), is present. Enantiomers differ by the direction they rotate polarized light: the amount of a chiral ...
Compounds with these properties consist of chiral molecules and are said to have optical activity. If a chiral molecule is dextrorotary, its enantiomer (geometric mirror image) will be laevorotary, and vice versa. Enantiomers rotate plane-polarized light the same number of degrees, but in opposite directions.
Of the three stereoisomers, two are enantiomers (levo- and dextro-2,3-butanediol) and one is a meso compound. [ 1 ] [ 2 ] The enantiomeric pair have (2 R , 3 R ) and (2 S , 3 S ) configurations at carbons 2 and 3, while the meso compound has configuration (2 R , 3 S ) or, equivalently, (2 S , 3 R ).
An enantiomeric pair (S,S)- and (R,R)-ethambutol, along with the achiral stereoisomer called meso-form, it holds a diastereomeric relationship with the optically active stereoisomers. The activity of the drug resides in the (S,S)-enantiomer which is 500 and 12 fold more potent than the (R,R)-ethambutol and the meso-form. The drug had initially ...
Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding the opposing enantiomer). Diastereomers have different physical properties (unlike most aspects of enantiomers) and often different chemical reactivity.
The stereochemical term enantiotopic refers to the relationship between two groups in a molecule which, if one or the other were replaced, would generate a chiral compound. The two possible compounds resulting from that replacement would be enantiomers. For example, the two hydrogen atoms attached to the second carbon in butane are enantiotopic.
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