A textbook of inorganic chemistry vol.VII part I Oxigen

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Musaev and coworkers also reexamined the possible involvement of the weakly bound hydrogen bonded structure, ž OH · · · ONOž , (Figure 6), arising from homolysis of HO−ONO that was first described by Houk and coworkers37e . However, it was soon discovered that at the Gibbs free-energy level, with entropy corrections, this weakly bound structure is not stable relž ative to the ž OH + ONO dissociation limit in the gas phase. It was also shown that the weak interaction between these radicals vanishes when increasing numbers of water molecules are explicitly included in the optimization.

This is distinctly different from the transition structures for dioxirane and peracid epoxidation where a spiro, but typically symmetrical, TS is observed. Additionally, the developing C−O bonds are considerably longer, indicating a more reactant-like structure in agreement with Hammond’s postulate. 104Å] C C FIGURE 17. 3 kcal mol−1 ] optimized at the B3LYP/6-311+G(d,p) level of theory. 9 kcal mol−1 48d 1. General and theoretical aspects of the peroxide group 37 Ethylene epoxidation with unsubstituted carbonyl oxide is ca 5 kcal mol−1 more exothermic than with dimethylcarbonyl oxide, yielding an even earlier transition state.

16 Robert D. 801] H H (d) FIGURE 4. Transition structures for the oxidation of trimethylamine (a), trimethylphosphine (b) and dimethyl sulfide (c,d) with peroxynitrous acid optimized at the B3LYP/6-311G**, MP2(full)/6-31G* (in parentheses) and QCISD/6-31G* (in brackets) levels 1. 876Å C N O O(HONO) FIGURE 5. B3LYP/6-311G(d,p) optimized intermediates and the transition structure for the reaction of ebselen with peroxynitrous acid. For details see Reference 40a A similar mechanistic dichotomy was suggested for the reactions of these two oxidants with a model compound of ebselen (1,2 benzisoselenazol-3(2H)-one)40b .

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