Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media

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	Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media
	Yi HP(易会萍) ; Wu J(吴江) ; Ding KL(丁奎岭) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭)
刊名	J. Org. Chem.
	2007
卷号	72 期号:3 页码:870-877
ISSN号	0022-3263
其他题名	氢键诱导的芳酰胺折叠体作为球苑类似物在水相中加速硝基取代的苯甲醚水解
通讯作者	黎占亭
英文摘要	Four intramolecular hydrogen bonding-driven aromatic amide foldamers 2-5 have been designed and synthesized in which a 2-methoxy-3-nitrobenzamide unit was incorporated at the end of the backbone. Kinetic studies in dioxane-water (4:1, v/v) at 60-90 degrees C have revealed that the folded backbone of the oligomers was, like the rigidified spherand, able to complex Li+, Na+, and K+ and, consequently, accelerated the hydrolysis of the nitro-appended anisole unit of the foldamers. Generally, longer foldamers displayed an increased accelerating effect, and LiOH displayed the highest reactivity probably due to the most efficient complexation by the folded oligomers. Addition of excessive potassium chloride substantially reduced the complexing interaction, and the hydrolysis of the longer oligomers became slower than that of the shorter ones due to an increased steric effect. The results indicate that, even in a hot aqueous medium of high polarity, intramolecular hydrogen bonding is still able to induce structurally matched oligomers to generate a preorganized rigidified conformation.
学科主题	物理有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo0619940
语种	英语
WOS记录号	WOS:000243735500024
公开日期	2013-01-16
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/12708]
专题	上海有机化学研究所_物理有机化学研究室
推荐引用方式 GB/T 7714	Yi HP,Wu J,Ding KL,et al. Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media[J]. J. Org. Chem.,2007,72(3):870-877.
APA	易会萍,吴江,丁奎岭,蒋锡夔,&黎占亭.(2007).Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media.J. Org. Chem.,72(3),870-877.
MLA	易会萍,et al."Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media".J. Org. Chem. 72.3(2007):870-877.