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How hydrogen-bonded MnO4- can influence oxidation of olefins in both gas phase and solution?
, Article Journal of Physical Organic Chemistry ; Volume 25, Issue 12 , 2012 , Pages 1198-1209 ; 08943230 (ISSN) ; Tehrani, Z. A ; Fattahi, A ; Hashemi, M. M ; Sharif University of Technology
2012
Abstract
The reaction pathway (including the transition state) of ethylene addition to permanganate (MnO4-) in the presence of ethylene glycol (EG) has been qualitatively and quantitatively studied by means of B3LYP/6-311++G* theoretical analysis. Interestingly, by cluster formation of the EG with permanganate, oxidation reaction becomes thermodynamically and kinetically more favorable. The influences of electron-withdrawing as well as electron-donating substituents were also explored. Results of the quantum theory of atoms in molecules and natural bond orbital analyses revealed that [3 + 2] addition reaction of alkenes in the presence of EG as hydrogen bonding donor to MnO4- becomes more exothermic....