异黄油酸的乙醇是异黄油酸的乙醇
Akkad Danho1, Artur Mardyukov1, Peter R Schreiner1
1Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, Giessen 35392, Germany. prs@uni-giessen.de.
概括
我们合成并鉴定了一种新型的醇,2-甲基--1--1,1-二醇,它是同黄油酸的高能体. 这种不稳定的乙醇重组为异黄油酸和二甲基基.
科学领域:
- 物理化学 物理化学
- 有机化学 有机化学
- 频谱学是一种光谱学.
背景情况:
- 异黄油酸是一种常见的碳素酸.
- 碳酸的高能分离体通常不稳定,难以合成.
- 对于反应机制来说,了解 tautomerization 路径至关重要.
研究的目的:
- 为了合成和表征异黄油酸的气相乙醇分离体.
- 为了研究合成的乙醇的稳定性和重新排列路径.
- 探索涉及乙醇及其分解产品的光化学反应.
主要方法:
- 合成2-甲基--1--1,1-二醇的气相合成.
- 在3.5K的低温子子矩阵隔离.
- 光谱表征 (例如,红外线,紫外线-Vis).
- 密度函数理论 (DFT) 的计算.
主要成果:
- 在基质矩阵中成功合成和分离2-甲基--1--1,1-二醇.
- 光谱数据和DFT计算证实了醇结构.
- 观察到埃诺的光化学重新排列到异黄油酸和二甲基基.
- 鉴定出烯可能是二甲基基的光化学产物.
结论:
- 2-甲基--1-烯-1,1-二醇是以前未报告的,高能质的异黄油酸体.
- 合成的乙醇是不稳定的,并经历光化学重组.
- 这项研究提供了对碳酸乙醇的反应性和分解途径的见解.
相关概念视频
Types of Enols and Enolates
2.6K
Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional...
2.6K
Reactivity of Enols
3.0K
Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
3.0K
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
4.3K
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
4.3K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
3.3K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.3K
Stereochemical Effects of Enolization
2.0K
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
2.0K
Regioselective Formation of Enolates
2.6K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
2.6K


