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Related Concept Videos

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...
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.
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...
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.
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.
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...

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

Are unsaturated isocyanides so different from the corresponding nitriles?

Anna Chrostowska1, Abdellatif Matrane, Daisuke Maki

  • 1Université de Pau et des Pays de l'Adour, CNRS, UMR 5254-IPREM-Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux, 2 avenue du Président Angot-Pau, 64053, France. anna.chrostowska@univ-pau.fr

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|December 17, 2011
PubMed
Summary

New synthesis of unsaturated isocyanides reveals strong electronic interaction between unsaturated groups and the isocyano moiety. This enhanced conjugation, studied via spectroscopy and calculations, offers insights into molecular orbital behavior.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Isocyanides are versatile organic compounds.
  • Understanding electronic interactions in unsaturated systems is crucial for molecular design.

Purpose of the Study:

  • To synthesize simple unsaturated and cyclopropylic isocyanides.
  • To investigate the electronic interplay between unsaturated moieties and the isocyano group.
  • To compare these interactions with corresponding nitriles.

Main Methods:

  • Efficient synthesis of isocyanides.
  • UV photoelectron spectroscopy.
  • Quantum chemical calculations.

Main Results:

  • The highest occupied molecular orbital (HOMO) ionization in unsaturated isocyanides involves the carbon-carbon multiple bond and the isocyanide π-system.
  • Ethenyl and ethynyl groups significantly destabilize the isocyano π-system, with ethenyl showing a stronger effect (3.12 eV) than cyano (2.70 eV).
  • Strong electronic conjugation was observed between the unsaturated moiety and the isocyanide group, evidenced by large energy gaps in photoelectron spectra.

Conclusions:

  • The study provides a facile synthetic route to unsaturated isocyanides.
  • Significant electronic conjugation exists between unsaturated carbon-carbon bonds and the isocyano group, exceeding that in analogous nitriles.
  • Photoelectron spectroscopy and computational methods effectively elucidate these electronic interactions.