Double-Proton Transfer in the Formamidine−Formamide Dimer. Post-Hartree−Fock Gas-Phase and Aqueous Solution Study

2002 ◽  
Vol 106 (50) ◽  
pp. 12103-12109 ◽  
Author(s):  
Yevgeniy Podolyan ◽  
Leonid Gorb ◽  
Jerzy Leszczynski
Keyword(s):  
Aqueous Solution ◽  
Proton Transfer ◽  
Gas Phase ◽  
Hartree Fock ◽  
Double Proton Transfer ◽  
Solution Study

Double-Proton Transfer in Adenine−Thymine and Guanine−Cytosine Base Pairs. A Post-Hartree−Fock ab Initio Study

2004 ◽  
Vol 126 (32) ◽  
pp. 10119-10129 ◽  
Author(s):  
Leonid Gorb ◽  
Yevgeniy Podolyan ◽  
Pawel Dziekonski ◽  
W. Andrzej Sokalski ◽  
Jerzy Leszczynski
Keyword(s):  
Proton Transfer ◽  
Ab Initio ◽  
Ab Initio Study ◽  
Base Pairs ◽  
Hartree Fock ◽  
Double Proton Transfer ◽  
Adenine Thymine

scholarly journals Diol Mediated Tautomerization of Glycine: a DFT Study

2019 ◽  
Vol 16 (1) ◽  
pp. 33-39
Author(s):  
Francis Suh ◽  
Vanessa Rivera ◽  
Ruben Parra
Keyword(s):  
Activation Energy ◽  
Aqueous Solution ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Gas Phase ◽  
Activation Energies ◽  
Dft Study ◽  
Hydroxyl Groups ◽  
Neutral Process ◽  
Product Forms

The tautomerization of glycine via a triple proton transfer was investigated both in the gas phase and in aqueous solution using the B3LYP/6-31+G(d,p) level of theory. Fully optimized complexes of the neutral and zwitterion forms of glycine with 1,3-propanediol were used for the reactant and product forms, respectively. The hydroxyl groups in the diol are conveniently oriented for glycine tautomerization through a concerted triple proton transfer facilitated by a network of three hydrogen bonds: N-H…O-H…O-H…O=C. The activation energy for the zwitterion à neutral process increases in solution. Also, the diol-glycine complex favors the neutral over the zwitterion form in a vacuum, but the opposite is true in solution. For comparative purposes, the tautomerization of glycine via a three-proton transfer mediated by two molecules of water was also examined. The results are qualitatively similar, albeit with activation energies that are smaller to those found in the corresponding diol-mediated tautomerization. KEYWORDS: Glycine; zwitterion, diol-mediated tautomerization; water-mediated tautomerization

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