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A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. [1][2] This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its mirror image (not to be confused with superimposable, as any two objects can ...
Chirality (chemistry) Two enantiomers of a generic amino acid that are chiral. (S)-Alanine (left) and (R)-alanine (right) in zwitterionic form at neutral pH. In chemistry, a molecule or ion is called chiral (/ ˈkaɪrəl /) if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational ...
[2] [3] Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds. [1] The number of hypothetical stereoisomers can be predicted by using 2 n, with n being the number of tetrahedral stereocenters; however, exceptions such as meso compounds can reduce the prediction to below the expected 2 n. [4]
Chirality(/kaɪˈrælɪti/) is a property of asymmetryimportant in several branches of science. The word chiralityis derived from the Greekχείρ(kheir), "hand", a familiar chiral object. An object or a system is chiralif it is distinguishable from its mirror image; that is, it cannot be superposed(not to be confused with superimposed) onto it.
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.
Chiral drugs. Chemical compounds that come as mirror-image pairs are referred to by chemists as chiral or handed molecules. [1] Each twin is called an enantiomer. Drugs that exhibit handedness are referred to as chiral drugs. Chiral drugs that are equimolar (1:1) mixture of enantiomers are called racemic drugs and these are obviously devoid of ...
The racemization occurs by way of an intermediate enol form in which the former stereocenter becomes planar and hence achiral. [14]: 373 An incoming group can approach from either side of the plane, so there is an equal probability that protonation back to the chiral ketone will produce either an R or an S form, resulting in a racemate.
A meso compound is superposable on its mirror image, therefore it reduces the number of stereoisomers predicted by the 2 n rule. This occurs because the molecule obtains a plane of symmetry that causes the molecule to rotate around the central carbon–carbon bond. [12] One example is meso-tartaric acid, in which (R,S) is the same as the (S,R) form