Simple and water-assisted tautomerism in succinimide

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• 作者：Younes Valadbeigi ; Hossein Farrokhpour
• 关键词：Succinimide ; Transition state structure ; Activation energy ; Water ; assisted tautomerism
• 刊名：Structural Chemistry
• 出版年：2015
• 出版时间：April 2015
• 年：2015
• 卷：26
• 期：2
• 页码：539-545
• 全文大小：1,209 KB
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• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

Isomerizations and tautomerisms in succinimide were studied using B3LYP and MP2 methods. Activation energies (E a) and Gibbs free energies of activation (?em class="a-plus-plus">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.