The nature of field effects and their fall-off with distance: the acidity of substituted quinuclidinium and bicyclooctylammonium ions was written by Adcock, W.;Anvia, F.;Butt, G.;Cook, A.;Duggan, P.;Grob, C. A.;Marriott, S.;Rowe, J.;Taagepera, M.. And the article was included in Journal of Physical Organic Chemistry in 1991.Application In Synthesis of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate This article mentions the following:
Gas-phase acidities are reported for a series of substituted quinuclidinium and bicyclo[2.2.2]octylammonium ions. Ab initio calculation are also reported for these equilibrium at the STO-3G and 3-21G (for the quinuclidines) bases and can be used to extend the results. PKa values obtained for the bicyclooctylammonium ions are compared with previously reported results for the quinuclidinium ions. The results, as a whole, are considered together with similar values obtained for other saturated systems, to look at the varying transmission of field effects with distance. The fall-off observed between the two series in the gas phase is considerably less than expected from simple electrostatics. In contradiction with a recent claim, it is also shown that field effects, as measured by the parameter σF, give a good measure of the effect of the substituents in each series compared with a combination of resonance and electronegativity effects. In the experiment, the researchers used many compounds, for example, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (cas: 135908-33-7Application In Synthesis of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate).
Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (cas: 135908-33-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Application In Synthesis of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics