Stereoisomerism

Stereoisomerism is the occurrence of compounds with the same molecular formula but different spatial arrangements, affecting drug action and activity.

  • Stereoisomerism is a form of isomerism in which molecules have:
  • The same molecular formula
  • The same sequence of bonded atoms (i.e., the same structural formula)
  • But a different spatial arrangement of atoms or groups in 3D space
  • So, unlike structural (constitutional) isomers, stereoisomers differ only in how atoms are oriented in space, not in how they’re connected.
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Classification of Stereoisomerism

  1. Geometrical Isomerism (cis-trans or E/Z)

    • Occurs due to restricted rotation (e.g., around double bonds or in cyclic systems)
    • Groups are arranged differently in space relative to a reference plane
    • Examples:
      • Cis-but-2-ene (same groups on the same side)
      • Trans-but-2-ene (same groups on opposite sides)
      • E/Z isomerism in alkenes with different substituents
  2. Optical Isomerism

    • Arises due to the presence of chiral centers or asymmetry
    • Molecules that can rotate plane-polarized light
    • Based on the concept of chirality

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