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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Diazonium Group Substitution: –OH and –H

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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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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Phase I Reactions: Reductive Reactions01:27

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Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Reductive Transformations of a Pyrazolate-Based Bioinspired Diiron-Dinitrosyl Complex.

Nicole Kindermann1, Anne Schober1, Serhiy Demeshko1

  • 1Institut für Anorganische Chemie, Georg-August-Universität Göttingen , Tammannstraße 4, 37077 Göttingen, Germany.

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|October 28, 2016
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Summary
This summary is machine-generated.

Researchers developed new diiron complexes that mimic bacterial nitric oxide reductases. These models help understand NO detoxification mechanisms, crucial for developing new antibacterial treatments against nitrosative stress.

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Area of Science:

  • Bioinorganic Chemistry
  • Coordination Chemistry
  • Enzyme Mechanisms

Background:

  • Flavo-diiron nitric oxide reductases (FNORs) detoxify nitric oxide (NO) in pathogenic bacteria, crucial for immune evasion.
  • Understanding FNOR mechanisms is key to developing novel antibacterial therapies.
  • Low molecular weight models for FNORs are scarce, limiting mechanistic studies.

Purpose of the Study:

  • To synthesize and characterize novel dinucleating pyrazolate/triazacyclononane hybrid ligand-based diiron complexes.
  • To investigate the nitrosyl adducts of these complexes as models for nonheme diiron active sites.
  • To explore the reductive transformation of nitrosyl adducts and compare them to biological systems.

Main Methods:

  • Synthesis of dinucleating pyrazolate/triazacyclononane hybrid ligand (L-).
  • Preparation of ferrous nitrile precursors and their conversion to nitrosyl adducts.
  • Spectroscopic characterization (UV-vis, IR, Mössbauer) and X-ray crystallography.
  • Electrochemical studies using cyclic voltammetry.
  • Stopped-flow IR spectroscopy for kinetic analysis.

Main Results:

  • Two novel diiron complexes with a pyrazolate/triazacyclononane hybrid ligand were synthesized.
  • Nitrosyl adducts ([L{Fe(NO)}2(μ-OOCR)](X)2, 2) were formed and spectroscopically characterized, resembling protein active sites.
  • Electrochemical reduction of nitrosyl adducts yielded a diiron tetranitrosyl complex and a diacetato-bridged ferrous complex, not N2O.
  • The tetranitrosyl complex product parallels suggested intermediates in methane monooxygenase hydroxylase decay.

Conclusions:

  • The developed diiron complexes serve as effective low molecular weight models for nonheme diiron active sites.
  • Reductive transformation of nitrosyl adducts leads to novel complexes, providing insights into NO detoxification pathways.
  • These findings contribute to understanding bacterial resistance mechanisms and inform the design of new therapeutic strategies.