By Matthew S. Platz, Robert A. Moss, Maitland Jones Jr.
The chemistry of reactive intermediates is important to a latest mechanistic and quantitative figuring out of natural chemistry. additionally, it underlies a good portion of recent man made chemistry and is crucial to a molecular view of organic chemistry. reports in Reactive Intermediate Chemistry provides an updated, authoritative advisor to this primary subject. even though it follows Reactive Intermediate Chemistry by means of an analogous authors, it serves as a free-standing source for the total chemical and biochemical neighborhood.
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In fact this nonexchange can be explained by Westheimer’s rules92 for pseudorotation, assuming the same rules apply to pentacoordinate sulfur. For the acid-catalyzed reaction, the likely intermediate would be 8 for which pseudorotation would be disfavored because it would put a carbon at an apical position. Further protonation to the cationic intermediate is unlikely even in 10 M HCl (the medium for Oae’s experiments) because of the high acidity of this species: a Branch and Calvin calculation124 (See Appendix), supplemented by allowance for the effect of the phenyl groups (taken as the difference in pKa between sulfuric acid and benzenesulfonic acid125), leads to a pKa of Ϫ7 for the ﬁrst pKa of this cation; about Ϫ2 for the second pKa, and about 3 for the third pKa.