ISL OpenIR  > 青海盐湖研究所知识仓储
Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(=O)YH (X = H, F, NH2, OH, CN, and CH3; Y = S, Se, and Te): A theoretical study
Huang, Genping2,3; Xia, Yuanzhi2,3; Li, Yahong1,2
2009-02-28
发表期刊JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
卷号896期号:1-3页码:80-84
文章类型Article
摘要Substituent effects on the conformational and energetic properties of keto-enol tautomerism of monochalcogenocarboxylic acids XC(=O)YH (X = H, F, NH2, OH, CN, and CH3; Y = S, Se, and Te) were investigated systematically by theoretical calculations. The relative stabilities of the tautomers, associated barrier heights and transition state geometries were reported. Results from different levels of calculations show that the keto forms are thermodynamically more stable than the enol forms by over 3 kcal/mol. Generally, compared with the H-substituted systems, the relative energies between the keto and enol isomers and activation energies of the keto-enol isomerizations are not affected much by the substituents NH2, CN, and CH3, which could form conjugations with the C=O group of the keto forms or the C=Y moieties of the transition states and enol forms. However, both the relative energies and activation energies would be increased by the strong electron-withdrawing substituents OH and F. The factors that influence the kinetic and thermodynamic properties of the tautomerizations were analyzed. Analysis of the transition state geometries show all these 1,3-H shift transition states are more similar to the products than the reactants, and the F- and OH-substituted ones are later than others. (C) 2008 Elsevier B.V. All rights reserved.
关键词Monochalcogenocarboxylic Acids Keto-enol Tautomerizations Substituent Effects Relative Stabilities Barrier Heights
WOS标题词Science & Technology ; Physical Sciences
关键词[WOS]RESONANCE RAMAN-SPECTROSCOPY ; UNIMOLECULAR PYROLYSIS MECHANISMS ; KETO-ENOL TAUTOMERIZATION ; IMINE-ENAMINE TAUTOMERISM ; REVERSIBLE-ARROW-ENAMINE ; AB-INITIO ; ORGANOSELENIUM COMPOUNDS ; RAY CRYSTALLOGRAPHY ; ACETYL DERIVATIVES ; NITRO TAUTOMERISM
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Physical
WOS记录号WOS:000263807800015
引用统计
文献类型期刊论文
条目标识符http://ir.isl.ac.cn/handle/363002/5912
专题青海盐湖研究所知识仓储
作者单位1.Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
2.Chinese Acad Sci, Qinghai Inst Salt Lakes, Xining 810008, Peoples R China
3.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714
Huang, Genping,Xia, Yuanzhi,Li, Yahong. Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(=O)YH (X = H, F, NH2, OH, CN, and CH3; Y = S, Se, and Te): A theoretical study[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,2009,896(1-3):80-84.
APA Huang, Genping,Xia, Yuanzhi,&Li, Yahong.(2009).Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(=O)YH (X = H, F, NH2, OH, CN, and CH3; Y = S, Se, and Te): A theoretical study.JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,896(1-3),80-84.
MLA Huang, Genping,et al."Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(=O)YH (X = H, F, NH2, OH, CN, and CH3; Y = S, Se, and Te): A theoretical study".JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM 896.1-3(2009):80-84.
条目包含的文件
条目无相关文件。
个性服务
推荐该条目
保存到收藏夹
查看访问统计
导出为Endnote文件
谷歌学术
谷歌学术中相似的文章
[Huang, Genping]的文章
[Xia, Yuanzhi]的文章
[Li, Yahong]的文章
百度学术
百度学术中相似的文章
[Huang, Genping]的文章
[Xia, Yuanzhi]的文章
[Li, Yahong]的文章
必应学术
必应学术中相似的文章
[Huang, Genping]的文章
[Xia, Yuanzhi]的文章
[Li, Yahong]的文章
相关权益政策
暂无数据
收藏/分享
所有评论 (0)
暂无评论
 

除非特别说明,本系统中所有内容都受版权保护,并保留所有权利。