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A molecule having exactly one chiral stereocenter (usually an asymmetric carbon atom) can be labeled (R) or (S), but a molecule having multiple stereocenters needs more than one label. For example, the essential amino acid L -threonine contains two chiral stereocenters and is written (2 S ,3 S )-threonine.
A chiral substance is enantioenriched or heterochiral when its enantiomeric ratio is greater than 50:50 but less than 100:0. [23] Enantiomeric excess or e.e. is the difference between how much of one enantiomer is present compared to the other.
[1] [2] Stereocenters are also referred to as stereogenic centers. A stereocenter is geometrically defined as a point (location) in a molecule; a stereocenter is usually but not always a specific atom, often carbon. [2] [3] Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds. [1]
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.
[1] [2] It is a rapid oscillation of the atom and substituents, the molecule or ion passing through a planar transition state. [3] For a compound that would otherwise be chiral due to a stereocenter , pyramidal inversion allows its enantiomers to racemize .
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]
In this approach: identify the chiral center, label the four atoms directly attached to the stereogenic center in question, assign priorities according to the sequence rule ( from 1 to 4), rotate the molecule until the lowest priority (number 4) substituent is away from the observer/viewer, draw a curve from number 1 to number 2 to number 3 ...
Enantiotopic groups are identical and indistinguishable except in chiral environments. For instance, the CH 2 hydrogens in ethanol (CH 3 CH 2 OH) are normally enantiotopic, but can be made different (diastereotopic) if combined with a chiral center, for instance by conversion to an ester of a chiral carboxylic acid such as lactic acid, or if coordinated to a chiral metal center, or if ...