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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature 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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic 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.
Structures of Carboxylic Acid Derivatives01:28

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...
Preparation of Amides01:29

Preparation 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...
Nomenclature of Primary Amines01:17

Nomenclature 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.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.

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Related Experiment Video

Updated: May 22, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

2-Cyano-2-methyl-propanamide.

Jia-Ying Xu, Wei-Hua Cheng

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2012
    PubMed
    Summary
    This summary is machine-generated.

    This study reveals the crystal structure of C(5)H(8)N(2)O, detailing how molecules form dimers through N-H⋯O hydrogen bonds. These dimers then assemble into zigzag chains along a specific crystallographic direction.

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    Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

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    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Understanding molecular interactions is crucial for predicting material properties.
    • Hydrogen bonding plays a significant role in the self-assembly of organic molecules.
    • The specific compound C(5)H(8)N(2)O has potential applications that warrant structural investigation.

    Purpose of the Study:

    • To determine the crystal structure of the title compound, C(5)H(8)N(2)O.
    • To elucidate the intermolecular interactions, specifically hydrogen bonding, governing the compound's solid-state arrangement.
    • To describe the supramolecular architecture formed by the molecules in the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to collect diffraction data.
    • The crystal structure was solved and refined using standard crystallographic software.
    • Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors and determining their geometric parameters.

    Main Results:

    • The crystal structure of C(5)H(8)N(2)O was successfully determined.
    • Molecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.
    • These inversion dimers are further connected by N-H⋯H hydrogen bonds, resulting in zigzag chains propagating along the [101] direction.

    Conclusions:

    • The crystal packing of C(5)H(8)N(2)O is dominated by a network of hydrogen bonds.
    • The formation of inversion dimers and subsequent zigzag chains dictates the overall supramolecular structure.
    • This detailed structural information provides a foundation for understanding the compound's physical and chemical properties.