一个稳定的N- heterocyclic carbene 与一个 diboron 骨干
Kelly E Krahulic1, Gary D Enright, Masood Parvez
1Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, T2N 1N4 Canada.
Journal of the American Chemical Society
|March 24, 2005
概括
研究人员合成了一种新型的五个成员无机环,一种稳定的N-异环碳与二博骨干. 这种新的碳联体与传统类似物相比,表现出增强的西格玛捐赠体特性.
科学领域:
- 有机金属化学 有机金属化学
- 无机化学 无机化学 有机化学
- 卡尔贝尼合物开发开发
背景情况:
- 在有机金属化学中,N-异环碳 (NHCs) 是关键的配体.
- 传统的NHC具有有机骨干,影响其电子和硬质性质.
- 探索无机骨干为调整碳联体行为提供了新的途径.
研究的目的:
- 为了合成和描述一种新的五个组成的无机环系统.
- 为了研究含有二博的N- heterocyclic carbene 的协调性质.
- 准备和研究一种含有这种新型碳联体的复合物.
主要方法:
- 一种基于二博的新型N-异环碳素前体的合成.
- 使用光谱技术进行表征 (NMR,IR,质谱).
- 进行X射线晶体学以确定前体,自由碳素和复合物的结构.
主要成果:
- 成功合成了一种稳定的五个成员无机环N- heterocyclic carbene与一个 diboron 骨干.
- 用新型碳联体形成一个五碳联体复合物.
- 光谱和结构数据显示,碳是一种强大的西格玛捐赠体,优于经典的NHCs.
结论:
- 迪博龙骨干显著增强了N-异环碳酸的西格玛捐赠能力.
- 无机脊柱为设计具有量身定制的协调性质的联体提供了强大的策略.
- 这项工作扩大了碳联体设计在有机金属化学中的范围.
相关概念视频
Carbocations
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Stability of Conjugated Dienes
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Removing one hydrogen from the intervening CH2 group with both...


