胺的盐形式:乙二甲的质子化
Harry S Jaconelli1, Alan R Kennedy1
1Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, United Kingdom.
Acta crystallographica. Section C, Structural chemistry
|August 8, 2024
概括
研究人员阐明了五种 hemi-protonated acetanilide 盐的结构. 氨基酸氧的质子化改变了键的长度和角度,通过键影响了晶体包装,为氨基酸化学提供了洞察力.
科学领域:
- 晶体学和结构化学
- 有机化学 有机化学
- 超分子化学 超分子化学
背景情况:
- 乙化 (N-甲) 是一种广泛研究的胺,具有药学意义.
- 了解胺的质子化行为对于药物设计和化学合成至关重要.
- 之前的研究已经探索了类似的化合物中的质子化,比如类醇.
研究的目的:
- 为了阐明五种半质子化乙化盐形式的晶体结构.
- 为了研究质子化对乙化物分子几何学和结合的影响.
- 为了比较阿塞塔尼利德的质子化效应与类醇的质子化效应.
主要方法:
- 单晶X射线衍射被用来确定半质盐的结构.
- 对键长度,键角度和键模式进行了分析.
- 不同盐形式和相关化合物之间的几何参数的比较.
主要成果:
- 五种 hemi-protonated acetanilide 盐的特征是成功的: 化物, 化物, 三化物, 四化物, 和 二氧化二氧化二氧化.
- 质子化发生在胺氧原子,导致延长的C=O键和缩短的C-N键.
- 结构具有由O-H...O键连接的中心对称二维单元,通过N-H...X相互作用形成1D链.
- 几何变化与半质子性青相似,但比完全质子性青更明显.
- 形状变化 (共平面与扭曲的胺基组) 影响结合角度的变化.
结论:
- 这项研究提供了详细的结构洞察力,了解了乙二的半质子化.
- 胺基质子会显著影响分子几何学和分子间相互作用.
- 这些发现有助于更深入地了解胺在酸性环境中的行为和晶体工程.
相关概念视频
01:19Amines to Amides: Acylation of Amines
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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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01:07Acid Halides to Amides: Aminolysis
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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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01:29Preparation of Amides
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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01:28Amides to Carboxylic Acids: Hydrolysis
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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
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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...
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