Quantum Chemical Conformational Analysis of 1,2-Ethanediol: Correlation and Solvation Effects on the Tendency To Form Internal Hydrogen Bonds in the Gas Phase and in Aqueous Solution

1994 ◽  
Vol 116 (9) ◽  
pp. 3892-3900 ◽  
Author(s):  
Christopher J. Cramer ◽  
Donald G. Truhlar
Keyword(s):  
Aqueous Solution ◽  
Hydrogen Bonds ◽  
Conformational Analysis ◽  
Gas Phase ◽  
Quantum Chemical ◽  
Solvation Effects ◽  
Internal Hydrogen

Pharmacophore modeling and conformational analysis in the gas phase and in aqueous solution of regioisomeric melatonin analogs. A theoretical and experimental study

2017 ◽  
Vol 1133 ◽  
pp. 534-545 ◽  
Author(s):  
Humberto Mendoza-Figueroa ◽  
Gelacio Martínez-Gudiño ◽  
Jorge E. Villanueva-Luna ◽  
Joel J. Trujillo-Serrato ◽  
Martha S. Morales-Ríos
Keyword(s):  
Aqueous Solution ◽  
Experimental Study ◽  
Conformational Analysis ◽  
Gas Phase ◽  
Pharmacophore Modeling

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

scholarly journals Спектры комбинационного рассеяния света глицина и их моделирование в дискретно-континуальной модели сольватной оболочки воды

2020 ◽  
Vol 128 (10) ◽  
pp. 1488
Author(s):  
И.В. Крауклис ◽  
А.В. Тулуб ◽  
А.В. Головин ◽  
В.П. Челибанов
Keyword(s):  
Aqueous Solution ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Raman Spectra ◽  
Quantum Chemical ◽  
Continuum Model ◽  
Good Description ◽  
Water Environment ◽  
Crystalline Form ◽  
Single Water Molecule

Annotation. The Raman spectra of glycine in crystalline form and in aqueous solution were obtained. The model of stabilization of the zwitterion state of glycine with a single water molecule connected by hydrogen bonds with the –COO- and –NH3+ groups is proposed. It is shown that quantum chemical calculations at the level of B3LYP/6-311++G(3df,2p) using the discrete-continuum model of water environment of glycine complexes Gly + n H2O (n = 1–3) provide a good description of the Raman spectra of glycine.

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