Enantiomers and Diastereomers

Both enantiomers and diastereomers are two different types of molecules that have the same molecular formula but different structural and physical properties from each other. Enantiomers are two identical compounds that have the same atoms and bonds between atoms in the carbon chain while diastereomers have the same number of carbon atoms but different arrangements or conformations of atoms.

What is Enantiomer?

Enantiomers are one of the types of molecules that have the same molecular formula but opposite arrangement of electrons on the carbon atom. They can be distinguished with nomenclature as double bond or single bond. For example :

Legend: [CC] means C=C double bond, Single or C-H bonds mean cis-trans isomer either right-handed or left handed.

Functions of Enantiomer

Enantiomers can be used to produce different effects when used in medicine, agro industry, and research.

Synthesis of Enantiomers

An enantiomer is an individual isomer that reflects the symmetry of the molecule but not the properties or other properties as compared to other diastereomers/enantiomers. Syntax of a desired ester which shows the direction of reaction is selected and then rearranged or strained by replacing atoms with their corresponding enantiomer.

Enantiopure Compounds

The synthesis of these esters is easily done by doing asymmetric synthesis giving high yields and purity. The synthesis of these esters is catalyzed by the use of chiral catalyst, enantiomeric excess, chiral auxiliary and reactant.

Merits of Enantiomers

Enantiomers have higher effects compared to racemic mixtures.

They have lower toxicity compared to diastereomers.

Enantiomers have different pharmacological effects compared to diastereomers such as sedation, hallucination, sleep and paralysis.

What are Diastereomers?

Diastereomers are one of the types of molecules that have the same molecular formula but they have different molecules with same atoms and bonds between atoms in the carbon chain. They can be distinguished by nomenclature as (+)- or (-)- or d- or l- isomers depending on the configuration at various stereocenters.

Functions of Diastereomers

They can be used as tools such as pharmaceuticals, agro products and research.

Synthesis of Diastereomers

Some of the asymmetric synthesis methods for synthesizing diastereomers include hydrolysis, oxa-reduction, gas chromatography, MALDI-MS and HPLC. The synthesis of these compounds are often assisted by chiral catalysts such as herbicidally produced allylic alcohols, epoxides and enantiomeric excess.

Merits of Diastereomers

Diastereomers have less effect compared to racemic mixtures.

They are often used as optical purity in synthetic drugs and the food industry.

They have different pharmacological effects compared to enantiomers such as stimulation and depressant.

Diastereomeric excess is the percent of one stereoisomer over the other. The ee value is always given in percent by adding the percent values for each enantiomer together. For example, if a compound contains 1% of one enantiomer and 99% of the other, its diastereomeric excess would be 98%.

Enantiomers and Diastereomers: Difference

1) Enantiomers having equal electronic configuration means that they have the same type of bonds between atoms in the carbon chain. They are highly potent active forms but weak inactive forms as a result of higher heat and light stability.

2) Enantiomeric pair is formed when both hydrogen atoms bonded with a carbon chain are the same so that they can be represented as C-H bonds but different arrangement of atoms in the chain will give different products therefore this result as diastereomer.

3) Enantiomers can be different in molecular formula and molecular weight.

4) Enantiomers have the same polarity, melting point and boiling point.

5) Both enantiomers and diastereomers are highly potent active forms but less potent inactive forms due to higher heat, light and chemical stability.

6) Enantiomers are more difficult to differentiate with nomenclature due to different stereochemistry but diastereomers are not so hard to distinguish with nomenclature.

7) Enantiopure compound is an individual isomer that reflects the symmetry of the molecule but not the properties or other properties as compared to other diastereomers or enantiomers.

8) Enantiomeric pairs can never be found in nature and synthetic enantiomerism.

9) Diastereomers can be used as tools such as pharmaceuticals, agro products and research.

10) Enantiomers are more difficult to synthesize than diastereomers.

Conclusion

Enantiomers and diastereomers are important for many industries because they are highly potent active forms but low inactive forms. Enantiomers are also important because they can be used as tools such as pharmaceuticals, agro products and research. Enantiomeric pair can never be found in nature and synthetic enantiomerism. Both enantiomers and diastereomers are highly potent active forms but less potent inactive forms due to higher heat, light and chemical stability. Lastly, both enantiopure compounds are high purity compounds with no double bonds.