vinylogy
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300px|thumb|Delocalization of negative charge in a generic carboxylate anion, derived from an organic carboxylic acid (cf. acetic acid), and the corresponding vinylogous carboxylate anion (the "vinylog/vinylogue" of the carboxylate anion), where a vinyl group now separates the charged oxygen from the [[carbonyl () group. The validity of the theoretical concept of vinylogy is supported by the pKa of such vinylogs, which approach that of the analogous carboxylic acid.]]
~5 min read
Article
3 sectionsContents
- Vinylogous reactivity
- Further reading
- References
300px|thumb|Delocalization of negative charge in a generic carboxylate anion, derived from an organic carboxylic acid (cf. acetic acid), and the corresponding vinylogous carboxylate anion (the "vinylog/vinylogue" of the carboxylate anion), where a vinyl group now separates the charged oxygen from the [[carbonyl () group. The validity of the theoretical concept of vinylogy is supported by the pKa of such vinylogs, which approach that of the analogous carboxylic acid.]]
In organic chemistry, vinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes. Formylacetone, technically , only exists in the ionized form or . Its adjectival form, vinylogous, is used to describe functional groups in which the standard moieties of the group are separated by a carbon–carbon double bond.