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首页> 美国卫生研究院文献>other >Dynamics for Reactions of Ion Pairs in Aqueous Solution: Reactivity of Tosylate Anion Ion Paired with the Highly Destabilized 1-(4-Methylphenyl)-222-Trifluoroethyl Carbocation
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Dynamics for Reactions of Ion Pairs in Aqueous Solution: Reactivity of Tosylate Anion Ion Paired with the Highly Destabilized 1-(4-Methylphenyl)-222-Trifluoroethyl Carbocation

机译：动力学在水溶液中离子对反应：甲苯磺酸酯阴离子离子配对的反应性与高度不稳定的1-（4-甲基苯基）-222-三氟乙基碳阳离子

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The sum of the rate constants for solvolysis and scrambling of carbon bridging and nonbridging oxygen-18 at 4-MeC6H4CH(CF3)OS(18O2)Tos in 50/50 (v/v) trifluoroethanol/water, (ksolv + kiso) = 5.4 × 10−6 s−1, is 50% larger than ksolv = 3.6 × 10−6 for the simple solvolysis reaction of the sulfonate ester. This shows that the ion pair intermediate of solvolysis undergoes significant internal return to form reactant. These data give a value of k−1 = 1.7 × 1010 s−1 for internal return of the carbocation-anion pair to the substrate. This rate constant is larger than the value of k−1 = 7 × 109 s−1 reported for internal return of an ion pair between the 1-(4-methylphenyl)ethyl carbocation and pentafluorobenzoate anion to the neutral ester (4-MeC6H4CH(CH3)O2CC6F5) in the same solvent. The partitioning of ion pairs to the 1-(4-methylphenyl)ethyl carbocation and to the highly destabilized 1-(4-methylphenyl)2,2,2-trifluoroethyl carbocation is compared and contrasted.

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