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Diastereomers are distinct molecular configurations that are a broader category. [3] They usually differ in physical characteristics as well as chemical properties. If two molecules with more than one chiral centre differ in one or more (but not all) centres, they are diastereomers. All stereoisomers that are not enantiomers are diastereomers.
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]
Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers that differ in all stereocenters and are therefore mirror images of one another. [3] Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding ...
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.
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As an example, four of the carbon atoms of the aldohexose class of molecules are asymmetric, therefore the Le Bel–Van 't Hoff rule gives a calculation of 2 4 = 16 stereoisomers. This is indeed the case: these chemicals are two enantiomers each of eight different diastereomers : allose , altrose , glucose , mannose , gulose , idose , galactose ...
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.
Stereoisomers have the same atoms or isotopes connected by bonds of the same type, but differ in the relative positions of those atoms in space. Two broad types of stereoisomers exist, enantiomes, and diastereomers. Enantiomers have identical physical properties but diastereomers do not. [7]