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Theoretical study of reaction of urea with methylamine: nucleophilic addition pathway

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Abstract

The B3LYP and wB97XD density functional methods were used to study the mechanisms and thermodynamic parameters of the activation and reactions of non-catalytic and catalyzed by phenol and p-toluenesulfonic acid reactions of urea with methylamine. The interaction proceeds stepwise with the intermediate formation of N-methylurea. The non-catalytic interaction has a large activation barrier. In the case of participation of methylamine dimer, the activation barrier decreases, but, nevertheless, remains high. During catalysis by phenol and p-toluenesulfonic acid, compounds exhibiting biphilic properties, the activation barrier decreases. The greatest decrease in the activation barrier is observed during catalysis with p-toluenesulfonic acid.

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The datasets used and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

All calculations were carried out at the Joint SuperComputer Center of the Russian Academy of Sciences—Branch of Federal State Institution «Scientific Research Institute for System Analysis of the Russian Academy of Sciences» (http://www.jscc.ru).

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  1. Institute of Polymers, Kazan National Research Technological University, Karl Marx street, 68, 420015, Kazan, Republic of Tatarstan, Russian Federation

    Ekaterina P. Kozhanova, Yakov D. Samuilov & Alexander Y. Samuilov

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Kozhanova, E.P., Samuilov, Y.D. & Samuilov, A.Y. Theoretical study of reaction of urea with methylamine: nucleophilic addition pathway. Theor Chem Acc 142, 132 (2023). https://doi.org/10.1007/s00214-023-03074-w

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