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Chiral molecules can differ in their chemical properties, but are identical in their physical properties, which can make distinguishing enantiomers challenging. Absolute configurations for a chiral molecule (in pure form) are most often obtained by X-ray crystallography , although with some important limitations.
For a chiral molecule with one or more stereocenter, the enantiomer corresponds to the stereoisomer in which every stereocenter has the opposite configuration. An organic compound with only one stereogenic carbon is always chiral. On the other hand, an organic compound with multiple stereogenic carbons is typically, but not always, chiral.
R-S isomerism of thalidomide. Chiral center marked with a star(*). Hydrogen (not drawn) is projecting behind the chiral centre. Enantiomers are molecules having one or more chiral centres that are mirror images of each other. [2] Chiral centres are designated R or S. If the 3 groups projecting towards you are arranged clockwise from highest ...
A configurational stereoisomer is a stereoisomer of a reference molecule that has the opposite configuration at a stereocenter (e.g., R- vs S-or E- vs Z-). This means that configurational isomers can be interconverted only by breaking covalent bonds to the stereocenter, for example, by inverting the configurations of some or all of the ...
In stereochemistry, an asymmetric carbon is a carbon atom that is bonded to four different types of atoms or groups of atoms. [1] [2] The four atoms and/or groups attached to the carbon atom can be arranged in space in two different ways that are mirror images of each other, and which lead to so-called left-handed and right-handed versions (stereoisomers) of the same molecule.
A chiral molecule is a type of molecule that has a non-superposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom. [16] [17] The term "chiral" in general is used to describe the object that is non-superposable on its mirror image. [18]
Chiral auxiliaries are one of many strategies available to synthetic chemists to selectively produce the desired stereoisomer of a given compound. [4] Chiral auxiliaries were introduced by Elias James Corey in 1975 [5] with chiral 8-phenylmenthol and by Barry Trost in 1980 with chiral mandelic acid. The menthol compound is difficult to prepare ...
Given a single, stereoisomerically pure starting material, a stereospecific mechanism will give 100% of a particular stereoisomer (or no reaction), although loss of stereochemical integrity can easily occur through competing mechanisms with different stereochemical outcomes.