Homoconjugated Carboxylic Acid Carboxylates

4 Tautomerizations Requiring Reorganization of the Environment 3SS Polar solvent + ion [Pg.355]

In an apolar environment, in the presence of weak interactions with a countercation, the charge prefers the residue exhibiting the higher electron delocalization. Polar [Pg.355]

Similar results have been obtained for homoconjugated anions of other carboxylic acids (inter- [72] and intramolecular [73]) and trimethylglycine TFA [74]. [Pg.356]

Tautomerization of Neutral Heterocyclic Acid-Base Complexes [Pg.356]

In mineral and synthetic engine oil formulations, hydrogen bond formation between anionic or molecular bases (A, B) and their conjugate acids HA or BH+, have a heavy impact on the activity of acids and their salts. For example, in mixtures of carboxylic acid with excess of sodium carboxylate in hydrocarbon and aprotic solvents, the activity of the acid is greatly decreased because of homoconjugation ... [Pg.113]

The expansion of the concept to encompass cyclic electron delocalization or homoaromaticity occurred in the late 1950s. In 1956 Applequist and Roberts pointed out that the cyclobutenyl cation resembles the cyclopropenium cation . Doering and colleagues suggested that the cycloheptatriene carboxylic acids could be regarded as planar pseudoaromatic type structures with a homoconjugative interaction between C(l) and C(6) . Based on the results of solvolytic studies on the bicyclo[3.1. OJhexyl system, Winstein set out the general concept of homoaromaticity in 1959 ... [Pg.413]

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