What is the Difference Between Lactam and Lactim?

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Lactams and lactims are organic compounds that are related to each other through a phenomenon called tautomerism. The key difference between them lies in their structure and the type of tautomerization they undergo:

  • Lactam: A lactam is a class of cyclic amides that are nitrogen analogues of lactones. They are formally derived from an amino alkanoic acid and are characterized by a cyclic structure with an amide group. Examples of lactams include β-propiolactam and γ-lactam.
  • Lactim: A lactim is a class of cyclic hydroxy-imides (enols) that are tautomeric with lactams. They are characterized by an endocyclic carbon-nitrogen double bond and are formed when lactams undergo tautomerization. Examples of lactims include β-propiolactim and γ-lactim.

The transformation between lactam and lactim forms is called lactam-lactim tautomerism, which is a special case of amide-imidol tautomerism. This tautomerism occurs due to the migration of a hydrogen atom within the molecule, leading to the formation of the imidic acid compound.

Comparative Table: Lactam vs Lactim

The main difference between lactam and lactim lies in their chemical structure and composition. Here is a table summarizing the differences between lactam and lactim:

Feature Lactam Lactim
Definition Lactam is a type of amide formally derived from an amino