Abstract
The mechanism to generate azomethine ylide from formaldehyde and glycine is systematically investigated. The density functional theory at the B3LYP/6-311++G(d,p) level is employed for both geometry optimization and single point energy calculation. Our results indicate that two possible pathways can lead to the generation of the carbinolamine intermediate with a favorable step-wise pathway. However, as for the step to form azomethine ylide, a concerted elimination of water and carbon dioxide is preferred. This calculation result is totally different from the widely accepted revised Rizzi mechanism.
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Original Russian Text © 2015 P. Wu.
The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1327-1331, November-December, 2015.
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Wu, P. Theoretical study of the mechanism generating azomethine ylide from formaldehyde and glycine. J Struct Chem 56, 1262–1267 (2015). https://doi.org/10.1134/S0022476615070057
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DOI: https://doi.org/10.1134/S0022476615070057