By George A. Olah
Superelectrophiles and Their Chemistry comprises, for the first-time, a dialogue of the fundamentals of this rising box of natural chemistry, along instruments to aid the reader observe the chemistry. particular instruments comprise an overview of the how one can raise the power of electrophiles, the category of superelectrophiles, the solvation concerns, a evaluation of tools for learning superelectrophilicity, with info of the superelectrophiles which have been pointed out and studied. additional info comprises substituent results in activation of superelectrophiles, and solvation in chemical reactions, in addition to an insightful check out destiny purposes.
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Extra resources for Superelectrophiles and Their Chemistry
The complex itself dissociates to the monocations, CHF2 + and H+ . When dicationic carbon tetrachloride is generated, the ion rearranges to a C2v structure thought to involve coordination of Cl2 and CCl2 2+ (67). Similarly, side-on coordination of O2 was proposed in the chromium complex 68. 45 When C7 H6 2+ is generated (from double ionization of toluene) and allowed to react with acetylene, new ions, C9 H7 2+ and C9 H6 2+ , are detected (eq 44). HC −2e− C6H5CH3 C7H6 2+ CH C9H72+ + C9H62+ (44) Experiments with deuterated species show extensive H/D scrambling, which implies longer-lived intermediates in the reaction.
These calculations have often involved the estimation of barriers to gas phase dissociation or deprotonation, and the proton afÞnities of conventional electrophilic intermediates. Other useful studies have calculated the heats of reactions for isodesmic processes. 37 kcal/mol + OH2 OH + + + 76 77 OH Transition State Structures Scheme 10. 81 + OH2 + 82 49 CALCULATIONAL METHODS enthalpy of reaction (eq 46). + H3C + C OH + OH C H3C H 83 ΔH°R = −160 kcal/mol + 46 + + CH4 CH3 (46) 84 It was concluded that separation of charge is the dominant driving force for the reaction.
Similar results were obtained with the benzoyl cation. Together with the results obtained from other work, these data suggest the formation of the protioacyl dications 46 and 47 in the highly acidic solutions. + H3C C O H + + + H3C C OH 46 + C O H + + + C OH 47 These examples illustrate how electrophilic systems can exhibit enhanced reaction rates and yields with increasing strength of the acidic reaction media. Both qualitative and quantitative kinetic studies strongly suggest the involvement of superelectrophilic species in reactions.