DFT explorations of tautomerism of 2-mercaptoimidazole in aqueous solution
Zhu, HJ ; Ren, Y ; Ren, J ; Chu, SY
Corresponding AuthorRen, Y (reprint author), Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China. yiren57@hotmail.com
AbstractA systematic investigation of the proton transfer in the tautomerization of 2-mercaptoimidazole was undertaken. Calculations in aqueous solution were performed using the combined supramolecular/continuum and the direct continuum models, respectively. Complexes containing one and two water molecules around the hydrophilic site of 2-mercaptoimidazole were used for the combined supramolecular/continuum calculation. DFT results predict that the barrier height for non-water-assisted intramolecular proton transfer is very high (175.8 kJ/mol). Hydrogen bonding between 2-mercaptoimidazole and the water molecule(s) will dramatically lower the barrier by the concerted multiple proton transfer mechanism. The proton transfer process through a eight-member ring formed by 2-mercaptoimidazole and two water molecules is found to be more efficient one and the calculated barrier height is reduced to ca. 72 kJ/mol. (c) 2005 Elsevier B.V. All rights reserved.
KeywordDft 2-mercaptoimidazole Tautomerism Water-assisted Proton Transfer Intramolecular Proton-transfer Direct-dynamics Solvent Glycine Solvation Spectra Models Equilibrium Continuum Cytosine
Subject AreaChemistry, Physical
Indexed Bysci
Document Type期刊论文
Recommended Citation
GB/T 7714
Zhu, HJ,Ren, Y,Ren, J,et al. DFT explorations of tautomerism of 2-mercaptoimidazole in aqueous solution[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,2005,730(1-3):199-205.
APA Zhu, HJ,Ren, Y,Ren, J,&Chu, SY.(2005).DFT explorations of tautomerism of 2-mercaptoimidazole in aqueous solution.JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,730(1-3),199-205.
MLA Zhu, HJ,et al."DFT explorations of tautomerism of 2-mercaptoimidazole in aqueous solution".JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM 730.1-3(2005):199-205.
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