Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction

doi:10.1002/chem.201602965

	Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction
	Gao, Yanan 3; Slattery, John M.2; Shimizu, Karina 4; Bruce, Duncan W.2; Canongia Lopes, Jose Nuno 1,4
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	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
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000387132800020
内容类型	期刊论文
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.