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Published on: November 23, 2016
2-Amino-2,3-dimethyl-butanamide.
1Department of Chemistry, Mudanjiang Teachers College, Mudanjiang 157012, People's Republic of China.
Summary
Researchers synthesized a novel compound, 2-amino-2,3-dimethyl-butanamide, using sulfuric acid. Crystallographic analysis revealed intermolecular hydrogen bonds linking its enantiomers in a unique 3D network.
Area of Science:
- Organic Chemistry
- Crystallography
- Chemical Synthesis
Background:
- Synthesis of novel organic compounds is crucial for developing new materials and pharmaceuticals.
- Understanding the structural properties of chiral molecules is essential in stereochemistry.
- Hydrogen bonding plays a significant role in molecular assembly and crystal engineering.
Purpose of the Study:
- To synthesize and characterize the novel compound 2-amino-2,3-dimethyl-butanamide.
- To elucidate the crystal structure of the racemic mixture of L- and R-2-amino-2,3-di-methyl-butanamide.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Chemical synthesis involving the reaction of 2-amino-2,3-dimethyl-butanonitrile with sulfuric acid (oil of vitriol).
- Single-crystal X-ray diffraction for crystallographic characterization.
- Analysis of intermolecular interactions, specifically hydrogen bonding.
Main Results:
- Successful synthesis of the target compound C(6)H(14)N(2)O.
- Determination of the crystal structure of a racemic mixture of L- and R-2-amino-2,3-di-methyl-butanamide.
- Identification of extensive inter-molecular N-H⋯O hydrogen bonds forming a three-dimensional network.
Conclusions:
- The synthesis route provides access to 2-amino-2,3-dimethyl-butanamide.
- The crystal structure reveals a specific hydrogen-bonding motif that organizes the enantiomers.
- This study contributes to the understanding of supramolecular assembly in chiral organic compounds.
Related Concept Videos
01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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.
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
01:19Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
01:29Preparation of Amides
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...
01:12Nomenclature of Secondary and Tertiary Amines
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...