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Structural Isomerism02:34

Structural Isomerism

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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...
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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

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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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Formation of Complex Ions03:45

Formation of Complex Ions

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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Nitrene transfer from a sterically confined copper nitrenoid dipyrrin complex.

Kurtis M Carsch1, Sasha C North2, Ida M DiMucci3

  • 1Department of Chemistry and Chemical Biology, Harvard University Cambridge MA 02138 USA betley@chemistry.harvard.edu.

Chemical Science
|October 13, 2023
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Summary

Researchers synthesized and characterized novel copper nitrenoid adducts supported by dipyrrin ligands. These intermediates enable efficient copper-catalyzed C-N bond formation via nitrene transfer reactions.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Copper-catalyzed nitrene transfer reactions are vital for forming carbon-nitrogen bonds.
  • Characterizing reactive intermediates in these processes remains challenging.

Purpose of the Study:

  • To synthesize and characterize novel copper nitrenoid adducts.
  • To investigate their spectroscopic properties and nitrene transfer capabilities.
  • To elucidate the mechanism of copper-mediated C-N bond formation.

Main Methods:

  • Synthesis of dipyrrin-supported copper(I) complexes.
  • Reaction with organoazides to form azide adducts.
  • Spectroscopic analysis (vibrational spectroscopy, X-ray diffraction).
  • Mechanistic studies including kinetic analysis and kinetic isotope effect measurements.
  • Density functional theory (DFT) and multiconfigurational calculations.

Main Results:

  • Isolation and characterization of stable copper nitrenoid adducts, proposed as triplet nitrene species.
  • Observation of stoichiometric and catalytic C-H amination and aziridination with perfluorinated arylazides.
  • Kinetic studies indicate rate-limiting copper nitrenoid formation.
  • Mechanistic insights suggest an electrophilic, enthalpically-controlled nitrene transfer pathway.

Conclusions:

  • The study provides direct characterization of key copper nitrenoid intermediates.
  • Elucidates the mechanism of copper-catalyzed nitrene transfer for C-N bond formation.
  • Offers a foundation for developing new catalytic methodologies in organic synthesis.