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Related Concept Videos

Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

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Related Experiment Video

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
09:10

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

4-Acetyl-3-(p-anis-yl)sydnone.

Hoong-Kun Fun, Wan-Sin Loh, Nithinchandra

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary

    This study details the crystal structure of 4-acetyl-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ium-5-olate. Four independent molecules were identified, with near-planar oxadiazole rings and specific dihedral angles to benzene rings, linked by hydrogen bonds.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Crystallographic studies are fundamental to understanding molecular structure and intermolecular interactions.
    • 1,2,3-oxadiazole derivatives are a class of heterocyclic compounds with diverse chemical properties.
    • The precise arrangement of molecules in a crystal lattice influences bulk material properties.

    Purpose of the Study:

    • To determine the crystal structure of 4-acetyl-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ium-5-olate.
    • To analyze the planarity of the 1,2,3-oxadiazole rings and their orientation relative to the benzene rings.
    • To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to elucidate the crystal structure.

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  • The asymmetric unit was analyzed to identify independent molecules and their spatial arrangements.
  • Intermolecular interactions, including C-H⋯O and C-H⋯N hydrogen bonds, were identified and characterized.

    • Main Results:

    • The asymmetric unit contains four crystallographically independent molecules of the title compound.
    • The 1,2,3-oxadiazole rings exhibit near-planarity with maximum deviations of 0.009 Å.
    • Dihedral angles between the oxadiazole and benzene rings range from 53.79° to 61.02°.
    • Intermolecular C-H⋯O and C-H⋯N hydrogen bonds link the molecules into sheets parallel to the (011) plane.

    Conclusions:

    • The crystal structure of 4-acetyl-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ium-5-olate has been fully characterized.
    • The observed planarity and dihedral angles provide insights into the electronic and steric properties of the molecule.
    • The identified hydrogen bonding network dictates the supramolecular architecture, influencing solid-state behavior.