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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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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.
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Diazonium Group Substitution: –OH and –H01:19

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
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Valence Bond Theory02:42

Valence Bond Theory

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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange
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Experimental and Computational Studies on Uranium Diazomethanediide Complexes.

Tongyu Li1, Dongwei Wang1, Yi Heng1

  • 1Department of Chemistry, Beijing Normal University, Beijing, 100875, China.

Angewandte Chemie (International Ed. in English)
|October 26, 2023
PubMed
Summary

Researchers synthesized novel uranium diazomethanediide complexes, revealing unique bonding and reactivity. These stable compounds offer insights into organometallic chemistry and potential applications.

Keywords:
ActinidesBondingDiazomethanediide ComplexesReactivityUranium

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Area of Science:

  • Organometallic Chemistry
  • Uranium Chemistry
  • Coordination Chemistry

Background:

  • Uranium imido compounds are versatile precursors in organometallic synthesis.
  • The exploration of novel ligands for f-element complexes remains an active area of research.

Purpose of the Study:

  • To synthesize and characterize new uranium diazomethanediide complexes.
  • To investigate the structural, electronic, and reactive properties of these novel complexes.

Main Methods:

  • Synthesis of uranium imido compounds.
  • Reaction with trimethylsilyl diazomethane to form diazomethanediide complexes.
  • Full characterization including X-ray crystallography.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Successful synthesis of the first isocyanoimido uranium complexes.
  • Demonstrated remarkable thermal stability of the synthesized compounds.
  • DFT studies revealed strong polarization and significant 5f orbital contribution in the U-NNC bonding.

Conclusions:

  • The novel uranium diazomethanediide complexes possess unique electronic structures.
  • Their reactivity includes nucleophilic behavior and [2+2] cycloaddition, highlighting their potential in synthetic chemistry.