Experimental and theoretical investigations on the tautomerism of 1-phenyl-2-thiobarbituric acid and its methylation reaction

	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
刊名	JOURNAL OF MOLECULAR STRUCTURE
	2013
卷号	1036 页码:372-379
关键词	1-Phenyl-2-thiobarbituric acid Tautomerism Methylation Quantum chemical calculation
英文摘要	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.
学科主题	Chemistry
收录类别	SCI
WOS记录号	WOS:000316091700049
公开日期	2016-05-03
内容类型	期刊论文
源URL	[http://ir.ihep.ac.cn/handle/311005/223960]
专题	中国科学院高能物理研究所
推荐引用方式 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.