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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.
C. Cahn–Ingold–Prelog priority rules; Capped octahedral molecular geometry; Capped square antiprismatic molecular geometry; Capped trigonal prismatic molecular geometry
Traditionally, double bond stereochemistry was described as either cis (Latin, on this side) or trans (Latin, across), in reference to the relative position of substituents on either side of a double bond. A simple example of cis–trans isomerism is the 1,2-disubstituted ethenes, like the dichloroethene (C 2 H 2 Cl 2) isomers shown below. [7]
Chiral resolution, or enantiomeric resolution, [1] is a process in stereochemistry for the separation of racemic mixture into their enantiomers. [2] It is an important tool in the production of optically active compounds, including drugs. [3]
Determining stereochemistry in atropisomers using the helicity rule follows the priority: front substituent A > backward substituent A > front substituent B > backward substituent B Determining the axial stereochemistry of biaryl atropisomers can be accomplished through the use of a Newman projection along the axis of hindered rotation.
An example of modest stereoselectivity is the dehydrohalogenation of 2-iodobutane which yields 60% trans-2-butene and 20% cis-2-butene. [5] Since alkene geometric isomers are also classified as diastereomers, this reaction would also be called diastereoselective.
In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. [ 1 ] [ 2 ] The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions.
E–Z configuration, or the E–Z convention, is the IUPAC preferred method of describing the absolute stereochemistry of double bonds in organic chemistry.It is an extension of cis–trans isomer notation (which only describes relative stereochemistry) that can be used to describe double bonds having two, three or four substituents.