Abstract
The effective charges and the proton affinity of carbon atoms of α-amino acids were calculated by quantum-chemical methods. The relative reactivity of the C−H bonds of amino acids under conditions of high-temperature solid-state catalytic isotope exchange (HSCIE) was studied. Correlations between the electron structure of amino acids and the regioselectivity of the solid-state isotope exchange were established. The reactivity of the carbon atoms with high proton affinity increases under HSCIE conditions. An assumption was made that the interaction of a solid organic compound with the spillover hydrogen can be described as the electrophilic substitution at the saturated and aromatic carbon atoms.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1611–1617, September, 1997.
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Zolotarev, Y.A., Laskatelev, E.V., Rozenberg, S.G. et al. Correlations between the quantum-chemical parameters of amino acids and regioselectivity of isotope exchange with the spillover hydrogen. Russ Chem Bull 46, 1536–1542 (1997). https://doi.org/10.1007/BF02502934
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DOI: https://doi.org/10.1007/BF02502934