Chemical Physics Letters
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The interaction between glycine and F2CO/F2SiO occurs through the formation of a π-tetrel bond between the C/Si atom and a carboxyl O atom. The interaction energy is some 20 kJ/mol for the C···O tetrel bond, but exceeds 300 kJ/mol for Si···O. As part of the latter complexation process, the proton engaged in the intramolecular OH··N H-bond is transferred across to the N, forming a zwitterion. This Si···O tetrel bond is more effective at inducing this proton transfer than is placement of the glycine in an aqueous medium, complexation with an anionic BH4-, or adding an electron to the glycine.
Hou, M., Li, Q., Scheiner, S. I. (2019). The ability of a tetrel bond to transition a neutral amino acid into a zwitterion. Chemical Physics Letters, 731, 136584. http://www.sciencedirect.com/science/article/pii/S000926141930555X
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