Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction
文献类型：期刊论文
| 作者 | Gao, Yanan3; Slattery, John M.2; Shimizu, Karina4; Bruce, Duncan W.2; Canongia Lopes, Jose Nuno1,4 |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2016-11-01 |
| 卷号 | 22期号:45页码:16113-16123 |
| 关键词 | Diels-alder Reaction Ionic Liquids Liquid Crystals Molecular Dynamics Simulations Ordered Solvents |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.201602965 |
| 文献子类 | Article |
| 英文摘要 | Liquid-crystalline ionic liquids (LCILs) are ordered materials that have untapped potential to be used as reaction media for synthetic chemistry. This paper investigates the potential for the ordered structures of LCILs to influence the stereochemical outcome of the Diels-Alder reaction between cyclopentadiene and methyl acrylate. The ratio of endo-to exo-product from this reaction was monitored for a range of ionic liquids (ILs) and LCILs. Comparison of the endo: exo ratios in these reactions as a function of cation, anion and liquid crystallinity of the reaction media, allowed for the effects of liquid crystallinity to be distinguished from anion effects or cation alkyl chain length effects. These data strongly suggest that the proportion of exo-product increases as the reaction media is changed from an isotropic IL to a LCIL. A detailed molecular dynamics (MD) study suggests that this effect is related to different hydrogen bonding interactions between the reaction media and the exo-and endo-transition states in solvents with layered, smectic ordering compared to those that are isotropic. |
| WOS关键词 | ROOM-TEMPERATURE ; ORGANIC-REACTIONS ; ENERGY RELATIONSHIPS ; MICELLAR CATALYSIS ; PHASE-BEHAVIOR ; SOLVENT ; WATER ; SALTS ; RATIONALIZATION ; ACCELERATION |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000387132800020 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169802]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 通讯作者 | Slattery, John M.; Bruce, Duncan W.; Canongia Lopes, Jose Nuno |
| 作者单位 | 1.Univ Nova Lisboa, Inst Tecnol Quim & Biol, Ave Republ, P-2780157 Oeiras, Portugal 2.Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England 3.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 4.Univ Lisbon, Inst Super Tecn, Ctr Quim Estrutural, Ave Rovisco Pais, P-1049001 Lisbon, Portugal |
| 推荐引用方式 GB/T 7714 | Gao, Yanan,Slattery, John M.,Shimizu, Karina,et al. Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction[J]. CHEMISTRY-A EUROPEAN JOURNAL,2016,22(45):16113-16123. |
| APA | Gao, Yanan,Slattery, John M.,Shimizu, Karina,Bruce, Duncan W.,&Canongia Lopes, Jose Nuno.(2016).Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction.CHEMISTRY-A EUROPEAN JOURNAL,22(45),16113-16123. |
| MLA | Gao, Yanan,et al."Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction".CHEMISTRY-A EUROPEAN JOURNAL 22.45(2016):16113-16123. |
入库方式： OAI收割
来源：大连化学物理研究所
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