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Isomer

physical science Maturity 11-13 Next article →

In the study of chemistry, molecules can be built from the exact same ingredients yet result in entirely different substances. These molecules are known as isomers. Isomerism describes the existence or possibility of these different forms. An isomer is a molecule or polyatomic ion that shares an identical molecular formula with another. This means they contain the same number of atoms of each element. However, these atoms are arranged differently in space. Because their shapes differ, isomers do not necessarily share similar chemical or physical properties.

IsomerOverview
IsomerOverview

The first major category is structural isomerism, also called constitutional isomerism. In these molecules, the atoms are connected by different chemical bonds. For instance, the molecular formula C3H8O can form three distinct compounds. One is 1-propanol, which has a chain of three carbon atoms with a hydroxyl group on the end. Another is 2-propanol, where the hydroxyl group is attached to the middle carbon. A third version is the ether methoxyethane, where an oxygen atom connects two separate carbon groups.

Structural isomers
Structural isomers

These variations in connection change the identity of the substance entirely.

Structural isomers can also vary in how their carbon chains are organized. Consider the hydrocarbon formula C3H4, which can form three different structures. Propadiene contains two double bonds in an open chain. Propyne uses one single bond and one triple bond. Finally, cyclopropene organizes its three carbon atoms into a ring using two single bonds and one double bond.

Propadiene structure
Propadiene structure
cyclopropene
cyclopropene

Some structural isomers are called tautomers. Tautomers are special because they can readily interconvert, meaning they exist in a state of equilibrium where they switch back and forth.

A second major category is stereoisomerism, or spatial isomerism. In stereoisomers, the atoms are connected by the same types of bonds. However, the relative positions of those atoms in three-dimensional space are different. Stereoisomerism is divided into two main types: enantiomers and diastereomers.

Stereoisomer are of two types, enantiomers vs diastereomers
Stereoisomer are of two types, enantiomers vs diastereomers

The depth of how scientists analyze these relationships can vary depending on the specific field of study.

Enantiomers are a specific type of stereoisomer that act like mirror images. A classic example is the molecule bromochlorofluoromethane. These molecules are described as chiral, meaning they have a handedness. Much like a left hand and a right hand, enantiomers cannot be made to coincide perfectly through simple rotation or translation. In many cases, changing one enantiomer into another would require breaking chemical bonds. Because of this, they are often viewed as different configurations. This is particularly important in biology. In living organisms, two enantiomers of a molecule like glucose can have very different roles.

2,3-pentadiene
2,3-pentadiene

Diastereomers are stereoisomers that are not enantiomers. One common form of this is cis-trans isomerism. This occurs when the arrangement of atoms is restricted by a rigid framework, such as a double bond or a ring. In dichloroethene, the chlorine atoms can be on the same side of a double bond, known as the cis isomer. Alternatively, they can be on opposite sides, known as the trans isomer.

Cisplatin and transplatin
Cisplatin and transplatin

This type of isomerism also appears in inorganic coordination compounds. For example, square planar molecules like cisplatin and transplatin show how the position of atoms changes the substance.

Even the types of atoms used can create new isomers through a process involving isotopes. An isotope is a version of an element with a different number of neutrons. If you replace a standard hydrogen atom with its isotope, deuterium, you can create new structural isomers. For example, in an ethane molecule, placing both deuterium atoms on the same carbon creates a different isomer than placing them on separate carbons. These are called isotopomers. These tiny changes in the atomic makeup can change how a molecule behaves in a microwave spectrum or how it reacts in a chemical environment.

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🖼️ Images & Media (9)
File:IsomerOverview.svg
IsomerOverview.svg
File:Structural isomers.svg
Structural isomers.svg
File:Propadiene structure.svg
Propadiene structure.svg
File:Propyne-2D-flat.png
Propyne-2D-flat.png
File:cyclopropene.png
cyclopropene.png
File:Stereoisomer are of two types, enantiomers vs diastereomers.svg
Stereoisomer are of two types,...
File:2,3-pentadiene.svg
2,3-pentadiene.svg
File:Cisplatin and transplatin.svg
Cisplatin and transplatin.svg
File:Cyclohexane chair form AND boat form 8254 TR.png
Cyclohexane chair form AND boat form 8254 TR.png
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