Mechanisms of Nucleophilic Substitution at the Carbon- Nitrogen Double Bond

碳-氮双键的亲核取代机制

• 批准号: 9214735
• 负责人: James Johnson
• 金额: $ 9.5万
• 依托单位: Texas Woman's University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1992
• 资助国家: 美国
• 起止时间: 1992-08-15 至 1996-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9214735&HistoricalAwards=false
• 关键词: Mechanisms; Nucleophilic; Substitution; Carbon; Nitrogen

This grant from the Organic Dynamics Program supports the work of Professor James E. Johnson at Texas Woman's University. The role of stereoelectronic effects in nucleophilic substitution reactions at the carbon-nitrogen double bond will be explored. Geometric isomers of imines will be synthesized, the rates of their reactions with oxygen and nitrogen nucleophiles will be measured, and the structures of the products will be determined. The specific studies that will be undertaken include: (1) nucleophilic substitution on cyclic hydroximates and hydroximoyl chlorides; (2) methoxide ion substitution on the Z and E isomers of n-propyl O-methylethoxy formohydroximate; (3) amine substitution in the Z and E isomers of hydroximoyl chlorides, and (4) hydrolysis of the Z and E isomers of a hydroximoyl tosylate and/or a hydroximoyl bromide. %%% The rates of reaction of several substrates that different in the arrangement of their atoms in space will be measured. Differences in reactivity and in the structures of the products will allow assessment of the effect of nonbonding electrons on the course of the reaction. The results of this study will contribute to an improved understanding of reactions of organic compounds which contain nitrogen atoms.

这项来自有机动力学项目的资助支持了这项工作 詹姆斯·E教授德克萨斯女子大学的约翰逊。 的 立体电子效应在亲核取代反应中的作用 将探索在碳-氮双键处的反应。 将合成亚胺的几何异构体， 它们与氧和氮亲核试剂的反应将是 测量，和产品的结构将是 测定 将进行的具体研究 包括：（1）环羟肟酸酯亲核取代 和肟酰氯;（2）甲氧基离子取代 正丙基O-甲基乙氧基Z和E异构体 甲羟肟酸;（3）Z和E异构体中的胺取代 的肟酰氯，和（4）水解的Z和E 羟肟基甲苯磺酸酯和/或羟肟基溴的异构体。 %%% 几种底物的反应速率不同， 它们的原子在空间中的排列将被测量。 反应性和产物结构的差异 将允许评估非成键电子对 反应的过程。 这项研究的结果将 有助于更好地理解有机反应 含有氮原子的化合物。