homoconjugation

https://doi.org/10.1351/goldbook.H02842
  1. [obsolete] Association between a base and its conjugate acid through a hydrogen bond ($\ce{B\bond{...}HB^{+}}$ or $\ce{AH\bond{...}A^{-}}$). Homoassociation is a more appropriate term for this phenomenon.
  2. The orbital overlap of two $\ce{\uppi\!\mbox{-}systems}$ separated by a non-conjugating group, such as $\ce{CH2}$.
See also: conjugate acid–base pair, conjugated system, homoaromatic
Source:
PAC, 1994, 66, 1077. (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1121 [Terms] [Paper]
Citation: 'homoconjugation' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.H02842 RIS BibTex EndNote
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