iminelike

Iminelike is an informal term in chemistry used to describe species whose structure or reactivity approximates an imine (a functional group containing a C=N bond). The label emphasizes similarity in electronic character—such as partial double-bond character at C=N, nucleophilic or electrophilic behavior at the carbon or nitrogen centers, or a propensity to participate in imine-like condensation or hydrolysis reactions—even when the group is not a classical neutral imine. Because 'iminelike' is not a formal IUPAC designation, its meaning varies with context and author. In practice, iminelike motifs appear in neutral or charged species including true imines, iminium ions (charged variants with C=N+), and related aza-analogs such as amidines or imino-enolates that can tautomerize to or from imine-like forms.

The term is commonly used in discussions of reaction mechanisms, catalysis, and computational studies to flag species that may act like imines in terms of reactivity or spectroscopy. For example, certain intermediates in organocatalysis and metal-catalyzed processes are described as iminelike when they bear C=N character that guides nucleophilic attack or electrophilic activation. Related concepts include imines, iminium ions, and aza-analog functional groups. The usage is therefore descriptive rather than defining a distinct class of compounds.