Stereoisomerism in organic chemistry involves molecules with the same molecular formula but different spatial atom arrangements, leading to unique properties. It includes geometric and optical isomerism, with significant implications in pharmaceuticals. Understanding chiral molecules and their enantiomers is crucial for drug efficacy and safety, as exemplified by the Thalidomide case. The complexity increases with multifunctional molecules, where the number of stereoisomers can be vast.
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Stereoisomerism refers to molecules with the same molecular formula but different three-dimensional arrangements of atoms
Distinct Properties
Stereoisomers can exhibit unique physical and chemical properties despite their structural similarities
The term 'stereoisomerism' is derived from the Latin and Greek words for solid, equal, and part, highlighting the concept of identical parts arranged differently
Understanding stereoisomerism is crucial in the pharmaceutical industry as the three-dimensional shape of a molecule can greatly affect its biological activity and pharmacological properties
Louis Pasteur first discovered stereoisomerism in 1848 when studying the properties of tartaric acid and its ability to rotate polarized light
There are two primary types of stereoisomerism: geometric and optical, which arise from different spatial arrangements of atoms
Geometric isomerism, also known as cis-trans isomerism, occurs in molecules with restricted rotation around double bonds or within cyclic structures
Optical isomerism occurs in molecules with chiral centers, resulting in non-superimposable mirror images called enantiomers
The concept of chirality and optical isomerism is crucial in biological systems, where specific three-dimensional shapes are necessary for biochemical processes
Alkenes can exhibit geometric isomerism, as seen in molecules like cis-2-butene and trans-2-butene
The spatial arrangement of atoms in a drug molecule can greatly impact its therapeutic effectiveness and potential for adverse effects, making stereoisomerism crucial in drug development
The case of Thalidomide highlights the importance of stereochemistry in ensuring drug safety, as different enantiomers can have different pharmacological effects and safety profiles
Structural isomerism involves molecules with the same molecular formula but differing in atom connectivity, while stereoisomerism pertains to different spatial arrangements of atoms within molecules
Structural isomerism can include variations in chain, positional, and functional group isomers
Multifunctional molecules with multiple chiral centers can have exponentially increasing numbers of stereoisomers, but the actual number may be less due to the presence of achiral meso compounds
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Definition of 'stereoisomerism'
Molecules with same molecular formula but different 3D atom arrangements.
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Importance of stereoisomerism in pharmaceuticals
3D shape of molecule influences biological activity and drug properties.
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Origin of the term 'stereoisomerism'
Derived from 'stereos' (solid), 'iso' (equal), 'meros' (part); denotes identical parts in different spatial configurations.
