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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.0K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Nitrosation of Enols

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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.
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Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
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...
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Color in Coordination Complexes
When atoms or molecules absorb light at the proper frequency, their electrons are excited to higher-energy orbitals. For many main group atoms and molecules, the absorbed photons are in the ultraviolet range of the electromagnetic spectrum, which cannot be detected by the human eye. For coordination compounds, the energy difference between the d orbitals often allows photons in the visible range to be absorbed and emitted, which is seen as colors by the human...
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Lewis Structures of Molecular Compounds and Polyatomic Ions02:54

Lewis Structures of Molecular Compounds and Polyatomic Ions

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To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
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Precipitation Reactions

50.0K
In a precipitation reaction, aqueous solutions of soluble salts react to give an insoluble ionic compound – the precipitate. The reaction occurs when oppositely charged ions in solution overcome their attraction for water and bind to each other, forming a precipitate that separates out from the solution. Since such reactions involve the exchange of ions between ionic compounds in aqueous solution, they are also referred to as double displacement, double replacement, exchange reactions, or...
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An Open-Shell FeIV Nitrido.

Jeewhan Oh1, Shao-Liang Zheng1, Kurtis M Carsch1

  • 1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society
|January 20, 2025
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Summary
This summary is machine-generated.

Researchers created a novel iron nitrido compound with a triplet ground state. This unique iron complex exhibits unprecedented reactivity, including C-H amination and C-C bond cleavage.

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Photocatalysis

Background:

  • Terminal iron nitrido complexes are crucial intermediates in nitrogen fixation and catalytic cycles.
  • Understanding the electronic structure of iron nitrido species is key to controlling their reactivity.
  • Previous studies have focused on low-spin iron nitrido analogues, limiting observed reactivity modes.

Purpose of the Study:

  • To photogenerate and characterize a novel open-shell, terminal iron nitrido complex.
  • To elucidate the electronic ground state and structural properties of the synthesized iron nitrido.
  • To explore the reactivity of this iron nitrido species, particularly in comparison to low-spin analogues.

Main Methods:

  • Synthesis and characterization of an iron nitrido complex using a sterically encumbered dipyrrin ligand.
  • Solid-state structural analysis and zero-field 57Fe Mössbauer spectroscopy.
  • Computational analysis to determine the electronic ground state and bonding characteristics.

Main Results:

  • Successful photogeneration and characterization of an open-shell, terminal iron nitrido complex, (EmL)Fe(N).
  • Evidence from structural data, Mössbauer spectroscopy, and computation indicates a triplet electronic ground state.
  • The iron nitrido complex displays attenuated Fe-N multiple bond character, enabling novel reactivity.

Conclusions:

  • The triplet ground state iron nitrido complex exhibits unique reactivity not seen in low-spin analogues.
  • This includes primary C(sp3)-H amination, H2 cleavage, aromatic C-C cleavage, and photocatalytic N-atom transfer.
  • This work expands the known reactivity landscape of iron nitrido compounds and opens new avenues in catalysis.