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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.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered ethane, the...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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Related Experiment Video

Updated: Jun 5, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

3-(1,3-Dioxoisoindolin-2-yl)propane-nitrile.

Xiao-Jun Li, Ming-Hui Xiong, Cheng-Cai Xia

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The crystal structure of C(11)H(8)N(2)O(2) was determined, revealing that intermolecular C-H⋯N and C-H⋯O interactions play a crucial role in stabilizing its crystal packing. This finding advances our understanding of molecular assembly in organic solids.

    Area of Science:

    • Crystallography
    • Solid-state chemistry
    • Supramolecular chemistry

    Background:

    • Understanding the factors that govern crystal packing is essential for predicting and controlling the solid-state properties of organic compounds.
    • Intermolecular interactions, such as hydrogen bonds and van der Waals forces, are key determinants of crystal lattice formation.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(11)H(8)N(2)O(2).
    • To identify and analyze the specific intermolecular interactions responsible for the observed crystal packing.
    • To contribute to the knowledge of structure-property relationships in organic crystalline materials.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure and arrangement in the solid state.

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  • Crystallographic analysis was performed to identify and quantify various intermolecular interactions, including C-H⋯N and C-H⋯O contacts.

    • Main Results:

    • The crystal structure of C(11)H(8)N(2)O(2) was successfully determined.
    • Analysis revealed the significant contribution of directed C-H⋯N and C-H⋯O interactions to the overall crystal packing.
    • These interactions act as stabilizing forces, consolidating the arrangement of molecules within the unit cell.

    Conclusions:

    • The crystal packing of C(11)H(8)N(2)O(2) is primarily stabilized by a network of C-H⋯N and C-H⋯O intermolecular interactions.
    • This study highlights the importance of weak hydrogen bonding interactions in supramolecular assembly and crystal engineering.
    • The findings provide valuable insights into the molecular design principles for creating novel organic materials with tailored solid-state properties.