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RESEARCH PRODUCT
On the tautomerization process of glycine in aqueous solution
Iñaki TuñónEstanislao SillaManuel F. Ruiz-lópezsubject
chemistry.chemical_classificationAqueous solutionGeneral Physics and AstronomyLimitingActivation energyTautomerAmino acidSolventchemistry.chemical_compoundchemistryComputational chemistryPolarizabilityZwitterionPhysical and Theoretical Chemistrydescription
The experimental activation energy for the tautomerization of glycine zwitterion neutral form has been reported to be 14.6 kcalrmol. It has been generally assumed that this energy barrier is needed for proton transfer to occur. However, previous theoretical results do not support this interpretation. In the present work, we examine this question using density functional calculations, extended basis sets and a polarizable continuum solvent model. Our results suggest that the limiting step for the tautomerization process corresponds basically to H-atom reorientation in the -COOH group. This could be a general feature in the tautomerization of amino acids. q 2000 Elsevier Science B.V. All rights reserved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2000-05-01 | Chemical Physics Letters |