By Henderson W. E.
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Extra resources for A Course in Inorganic Preparations
This prompted the suggestion by Houk and coworkers 37e that the hydroxyl radical is formed in a tight cage in aqueous solution, still capable of performing one-electron oxidations. Two-electron oxidations (oxygen atom transfer) of amines, sulfides26b and selenides46 by HO−ONO have been observed experimentally. Earlier theoretical studies by Houk and coworkers37e suggest that HO−ONO should provide oxidative reactivity comparable to that of organic peroxyacids. Transition structures were located for the concerted peroxynitrous acid oxidations of H2 S, NH3 and ethylene.
This transition structure differs markedly from that found for neutral HO−ONO; the transition structure is highly asymmetrical. This is a nucleophilic addition transition state, and the second phase of the reaction would involve cyclization of the oxirane ring and expulsion of NO2 − . This reaction would be especially facile for electron-deficient alkenes, analogous to the Michael-type epoxidation of enones by basic hydrogen peroxide. The oxidation of the more nucleophilic amines and sulfides, on the other hand, will be highly disfavored.
The relative energetics and isomerization barriers for dimethyldioxirane were also computed in that study with relatively large basis sets. 2 kcal mol−1 with the inclusion of zero-point vibrational energy (ZPVE) corrections. 5 kcal mol−1 at the same level of theory. The molecular structure of dimethylsubstituted carbonyl oxide has Cs symmetry with a staggered conformation. 28 A bond character, which implies that the electronic structure of dimethylcarbonyl oxide prefers the zwitterionic form. The transition state for the cyclization of dimethyl carbonyl oxide to dimethyldioxirane has C1 symmetry (Figure 15)79 .
A Course in Inorganic Preparations by Henderson W. E.