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Experimental and theoretical investigations on the tautomerism of 1-phenyl-2-thiobarbituric acid and its methylation reaction
Wang, G; Wang, J; Nie, H; Tan, SP; Shi, WQ; Zhao, DM; Cheng, MS;石伟群
2013
发表期刊JOURNAL OF MOLECULAR STRUCTURE
卷号1036页码:372-379
摘要In the present study, 1-phenyl-2-thiobarbituric acid (1) was synthesized and the tautomerism of this compound was investigated by FT-IR spectroscopy, X-ray analysis and H-1 NMR study as well as quantum chemical calculations. It is found that compound 1 exists in triketo form in the solid state and in CDCl3 solution while tautomerization was observed in DMSO-d(6), DMF-d(7) and CD3OD solution. The geometry optimization of eight possible tautomers of 1-phenyl-2-thiobarbituric acid was performed in gas phase and in different solvents using COSMO method. The calculated results are in good accordance with experimental data. Additionally, the methylation reaction of 1-phenyl-2-thiobarbituric acid was investigated for the first time by combination of experimental and theoretical methods. The methylation product might be varied with three possible isomers because of the structural features of 1-phenyl-2-thiobarbituric acid. We identified the obtained methylation product by X-ray diffraction and FT-IR spectroscopy, and transition state search and energy calculation were conducted to elucidate experimental data, the results revealed that the theoretical calculations are consistent with experimental data. (c) 2012 Elsevier B.V. All rights reserved.
关键词1-Phenyl-2-thiobarbituric acid Tautomerism Methylation Quantum chemical calculation
学科领域Chemistry
DOI10.1016/j.molstruc.2012.12.017
收录类别SCI
WOS记录号WOS:000316091700049
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被引频次:1[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.ihep.ac.cn/handle/311005/223960
专题多学科研究中心
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GB/T 7714
Wang, G,Wang, J,Nie, H,et al. Experimental and theoretical investigations on the tautomerism of 1-phenyl-2-thiobarbituric acid and its methylation reaction[J]. JOURNAL OF MOLECULAR STRUCTURE,2013,1036:372-379.
APA Wang, G.,Wang, J.,Nie, H.,Tan, SP.,Shi, WQ.,...&Cheng, MS;石伟群.(2013).Experimental and theoretical investigations on the tautomerism of 1-phenyl-2-thiobarbituric acid and its methylation reaction.JOURNAL OF MOLECULAR STRUCTURE,1036,372-379.
MLA Wang, G,et al."Experimental and theoretical investigations on the tautomerism of 1-phenyl-2-thiobarbituric acid and its methylation reaction".JOURNAL OF MOLECULAR STRUCTURE 1036(2013):372-379.
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