Advances in Physical Organic Chemistry by John P. Richard (Eds.)

By John P. Richard (Eds.)

Advances in actual natural Chemistry offers the chemical group with authoritative and demanding checks of the various facets of actual natural chemistry. the sector is a quickly constructing one, with effects and methodologies discovering software from biology to stable country physics. * experiences the appliance of quantitative and mathematical tools in the direction of knowing chemical difficulties * Multidisciplinary volumes conceal natural, organometallic, bioorganic, enzymes and fabrics themes

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If pKR was converted to HIA, pKH2 O in the cycle would be replaced by the energy of hydrogenation. The latter provides the conventional measure of double bond stability, save that here free energy in aqueous solution is measured rather than the more usual heat of hydrogenation in the gas phase. We will return to a comparison of values of these equilibrium constants for different carbocations, but first pursue pKa and pKR for the benzenonium ion. In azide buffers this cation reveals no trapping by azide ion.

2 makes the vinyl cation the most unstable carbocation for which equilibrium measurements are available. It is remarkable that while the vinyl cation and benzenonium ion have similar pKas, their pKR values differ by 38 log units. This is an indication of the sensitivity of pKa to the stability of the conjugate base of the cation, and specifically to the very different energies of p-bonds in acetylene and benzene. 118 Thus Lucchini and Modena’s access to the parent vinyl cation clearly depends on the high energy of the triple bond of their alkyne reactant.

It might seem surprising that a nucleophilic reaction with water competes with proton loss from the phenanthrenonium ion considering the stability of the aromatic product. As discussed by Richard24 (and considered further below) this reflects a higher intrinsic reactivity of the cations toward nucleophilic attack which compensates for the thermodynamic disadvantage of this reaction. 75 In all these cases it is possible to determine KR directly by combining kH2 O with kH, the rate constant for carbocation formation.

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