Abstract
Isomerizations and tautomerisms in succinimide were studied using B3LYP and MP2 methods. Activation energies (E a) and Gibbs free energies of activation (∆G #) were calculated for O–H rotations, keto–enol, and amine–imine tautomerisms. The calculated activation energies for the O–H rotations were generally smaller than 30 kJ/mol and for keto → enol and amine → imine tautomerisms were about 300 and 210 kJ/mol, respectively. Water molecules were used to catalyze the proton transfer reactions in the keto–enol and amine–imine tautomerisms. It was found that water molecules decrease the activation energies of the tautomerisms. Also, catalytic effect of two water molecules was more than that of one water molecule.
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The authors wish to express thanks to the Center of Excellency in Chemistry of Isfahan University of Technology.
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Valadbeigi, Y., Farrokhpour, H. Simple and water-assisted tautomerism in succinimide. Struct Chem 26, 539–545 (2015). https://doi.org/10.1007/s11224-014-0511-6
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DOI: https://doi.org/10.1007/s11224-014-0511-6