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In stereochemistry, an epimer is one of a pair of diastereomers. [1] The two epimers have opposite configuration at only one stereogenic center out of at least two. [2] All other stereogenic centers in the molecules are the same in each. Epimerization is the interconversion of one epimer to the other epimer.
For example, despite having chiral gauche conformers that belong to the C 2 point group, butane is considered achiral at room temperature because rotation about the central C–C bond rapidly interconverts the enantiomers (3.4 kcal/mol barrier). Similarly, cis-1,2-dichlorocyclohexane consists of chair conformers that are nonidentical mirror ...
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. [1] The study of stereochemistry focuses on the relationships between stereoisomers, which are defined as having the same molecular formula and sequence of bonded atoms (constitution) but differing in the geometric positioning of the atoms in space.
Le Bel-van't Hoff rule states that for a structure with n asymmetric carbon atoms, there is a maximum of 2 n different stereoisomers possible. As an example, D-glucose is an aldohexose and has the formula C 6 H 12 O 6. Four of its six carbon atoms are stereogenic, which means D-glucose is one of 2 4 =16 possible stereoisomers. [20] [21]
One of the first such racemates studied, by Pasteur in 1853, forms from a 1:2 mixture of the bis ammonium salt of (+)-tartaric acid and the bis ammonium salt of (−)-malic acid in water. Re-investigated in 2008, [ 9 ] the crystals formed are dumbbell -shape with the central part consisting of ammonium (+)-bitartrate, whereas the outer parts ...
[4] [5] The configuration of other chiral compounds was then related to that of (+)-glyceraldehyde by sequences of chemical reactions. For example, oxidation of (+)-glyceraldehyde (1) with mercury oxide gives (−)-glyceric acid (2), a reaction that does not alter the stereocenter. Thus the absolute configuration of (−)-glyceric acid must be ...
A molecule with an integer n describing the number of stereocenters will usually have 2 n stereoisomers, and 2 n−1 diastereomers each having an associated pair of enantiomers. [3] [4] The CIP sequence rules contribute to the precise naming of every stereoisomer of every organic molecule with all atoms of ligancy of fewer than 4 (but including ...
In chemistry, dynamic stereochemistry studies the effect of stereochemistry on the reaction rate of a chemical reaction. Stereochemistry is involved in: