By John P. Richard (Eds.)
Advances in actual natural Chemistry offers the chemical group with authoritative and significant exams of the various elements of actual natural chemistry. the sphere is a swiftly constructing one, with effects and methodologies discovering program from biology to stable nation physics. * studies the applying of quantitative and mathematical equipment in the direction of realizing chemical difficulties * Multidisciplinary volumes disguise natural, organometallic, bioorganic, enzymes and fabrics issues
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134–136 Estimates of pKR for representative methoxy and dimethoxy carbocations are shown in the first two rows of structures at the bottom of the page. The structures and pKR values shown summarize the influence on carbocation stability of (a) accumulating methoxy substitution, (b) the difference between methoxy and ethoxy substituents and between cyclic and acylic structures (with five-membered ring cyclic structures indicated as (CH2O)2C+R) and (c) the influence of methyl and phenyl substituents.
5. In so far as values of pKH2 O for the hydration of alkenes are known or can be estimated,47 values of pKR can be derived by combining rate constants for protonation of alkenes with the reverse deprotonation reactions of the carbocations. The protonation reactions seem much less likely to be concerted with attack of water on the alkene than the corresponding substitutions. 0Â108 sÀ1 for deprotonation of the t-butyl cation75 by combining Ka with the measured rate constant for the hydration of butene,86 for which protonation of the alkene is rate-determining.
The latter behavior implies that the unfavorable effect of benzoannelation on the stability of the reacting double bond of the aromatic molecules is greater than that on the stability of the carbocations. Ph + Me Me 18 Cox’s extrapolation of rate constants for protonation of a number of ringsubstituted benzenes72 can be combined with the correlation of Fig. 1 to derive pKas in the same way as for benzene and naphthalene. 0. Cox noted the activating effect of bromine on hydrogen isotope exchange, which is partially concealed by a statistical factor of six which increases the basicity of benzene.