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首页> 外文期刊>ACS Omega >Effects of Solvent Polarity on the Reaction of Aldehydes and Ketones with a Hydrazide-Bound Scavenger Resin
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Effects of Solvent Polarity on the Reaction of Aldehydes and Ketones with a Hydrazide-Bound Scavenger Resin

机译:溶剂极性对酰肼和酮与酰肼结合清除树脂反应的影响

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摘要

Polymer-supported reagents have been extensively studied and used in various applications, such as condensation reactions and multiple component reactions. This paper examines the reactions between a solid-functionalized resin, named Amb15-Iso, and aldehydes and ketones that have been solubilized in different solvents. The reactions between these molecules and a hydrazide (isoniazid) in both neutral and acidic media were also studied. The results showed that the solvent polarity influenced the kinetics of the reaction and the yields of carbonyl compounds that were captured by the resin, particularly, for less-reactive molecules. The reactions using the resin were faster than those using free isoniazid in solution, likely because the acidic sites remaining in the resin can catalyze the reaction, increasing the rate of capture. A high dependence on the presence of acidic compounds and the rate of the reaction was observed, in which trifluoroacetic acid was used to catalyze the reaction between the tested molecules and isoniazid in solution. The differential reactivities of the examined ketones and aldehydes in these condensation reactions demonstrate that the resin can provide selective criteria, preferentially scavenging aldehydes from solution. While benzaldehyde reacted quite quickly with the resin, acetophenone barely had any reaction and remained in solution.
机译:已经广泛地研究了聚合物 - 负载的试剂,并用于各种应用,例如缩合反应和多种组分反应。本文研究了在不同溶剂中溶解的固体官能化树脂,名为AMB15-ISO和醛和酮之间的反应。还研究了这些分子和酰肼(异氮化物)在中性和酸性培养基中的反应。结果表明,溶剂极性影响了反应的动力学和由树脂捕获的羰基化合物的产率,特别是对于较少反应分子。使用树脂的反应比在溶液中使用的游离异烟肼的反应更快,可能因为残留在树脂中的酸性位点可以催化反应,增加捕获率。观察到对酸性化合物的存在和反应速率的高依赖性,其中三氟乙酸用于催化测试分子与异烟肼之间的反应。在这些缩合反应中检测的酮和醛的差异反应表明树脂可以提供选择性标准,优先清除来自溶液的醛。苯甲醛与树脂相当快地反应,苯酮几乎没有反应并保持在溶液中。

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