Confinement as a Tool in Chemistry: Accelerated Intracapsular Dimerization of Cyclopentadiene in Water

IF 2.3 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Amal Sam Sunny, Prof. Vaidhyanathan Ramamurthy
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引用次数: 0

Abstract

In this study, the occurrence of Diels–Alder reaction of cyclopentadiene yielding dicyclopentadiene within a confined closed space provided by octa acid (OA) in water at room temperature is established. The Diels–Alder reaction within the OA capsule occurs at least 2000 times faster than in water. Catalysis of Diels–Alder reaction by hosts such as cyclodextrin, cucurbituril, and Fujita's Pd nano–host occurs in water. Despite their similarity, these three hosts provide an open environment where the reactant molecules are exposed to aqueous environment. The only fully closed host known to catalyze the Diels–Alder reaction in water is OA. Although Rebek's host is established to catalyze Diels–Alder reaction it occurs in an organic solvent. The closed environment explored in this presentation provides an opportunity to better understand the origin of non–covalent catalysis in a restricted space and in water. Because the product binds stronger than the reactant, disappointingly, the capsule can't be recycled. We recognize that this aspect needs to be addressed for the OA capsule to become synthetically useful. We are in the process of understanding the origin of catalysis and finding ways to make reaction recyclable.

作为化学工具的封闭:环戊二烯在水中的加速囊内二聚反应
本研究证实,在室温下,环戊二烯在辛酸(OA)提供的密闭空间内发生 Diels-Alder 反应,生成二环戊二烯。在 OA 胶囊内发生的 Diels-Alder 反应比在水中至少快 2000 倍。环糊精、葫芦素和藤田钯纳米宿主等宿主在水中催化 Diels-Alder 反应。尽管它们很相似,但这三种宿主提供了一个开放的环境,使反应物分子暴露在水环境中。已知唯一能在水中催化 Diels-Alder 反应的全封闭宿主是 OA。虽然 Rebek 的宿主可以催化 Diels-Alder 反应,但它是在有机溶剂中发生的。本报告探讨的封闭环境为我们提供了一个机会,使我们能够更好地了解在受限空间和水中非共价催化作用的起源。令人失望的是,由于生成物比反应物的结合力更强,胶囊无法循环使用。我们认识到,要使 OA 胶囊在合成方面发挥作用,就必须解决这个问题。我们正在了解催化的起源,并寻找使反应可回收的方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Israel Journal of Chemistry
Israel Journal of Chemistry 化学-化学综合
CiteScore
6.20
自引率
0.00%
发文量
62
审稿时长
6-12 weeks
期刊介绍: The fledgling State of Israel began to publish its scientific activity in 1951 under the general heading of Bulletin of the Research Council of Israel, which quickly split into sections to accommodate various fields in the growing academic community. In 1963, the Bulletin ceased publication and independent journals were born, with Section A becoming the new Israel Journal of Chemistry. The Israel Journal of Chemistry is the official journal of the Israel Chemical Society. Effective from Volume 50 (2010) it is published by Wiley-VCH. The Israel Journal of Chemistry is an international and peer-reviewed publication forum for Special Issues on timely research topics in all fields of chemistry: from biochemistry through organic and inorganic chemistry to polymer, physical and theoretical chemistry, including all interdisciplinary topics. Each topical issue is edited by one or several Guest Editors and primarily contains invited Review articles. Communications and Full Papers may be published occasionally, if they fit with the quality standards of the journal. The publication language is English and the journal is published twelve times a year.
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