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Related Concept Videos

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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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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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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 Enols01:19

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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Rate-Determining Steps03:08

Rate-Determining Steps

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Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Nitrite Formation at a Diiron Dinitrosyl Complex.

Anna L Poptic1, Jeffrey K Klinger1, Samantha L Carter1

  • 1Department of Chemistry & Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio43210, United States.

Journal of the American Chemical Society
|October 10, 2023
PubMed
Summary
This summary is machine-generated.

This study presents a novel synthetic diiron complex that mimics the nitric oxide (NO) oxidizing activity of a bacterial enzyme. The model complex successfully converts NO to nitrite, offering insights into bacterial immune evasion mechanisms.

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Area of Science:

  • Bioinorganic Chemistry
  • Enzyme Mimicry
  • Bacterial Pathogenesis

Background:

  • Pathogenic bacteria utilize iron-containing enzymes to detoxify nitric oxide (NO), a mammalian immune molecule.
  • Flavodiiron nitric oxide reductases (FNORs) and hemerythrin-like proteins (HLPs) are key bacterial enzymes involved in NO metabolism.
  • While FNORs reduce NO, certain HLPs like Mka-HLP oxidize NO to nitrite, a function not yet replicated by synthetic models.

Purpose of the Study:

  • To synthesize a novel diiron complex modeling the electron-poor active site of Mka-HLP.
  • To investigate the nitric oxide (NO) oxidation reactivity of this synthetic complex.
  • To provide the first synthetic model replicating the NO oxidase activity observed in Mka-HLP.

Main Methods:

  • Synthesis of a new diiron complex designed to mimic the electron-poor coordination environment of Mka-HLP.
  • Reaction of the diferrous precursor with nitric oxide (NO) to form diiron dinitrosyl and mononitrosyl species.
  • Isolation, characterization, and functional testing of the resulting nitrosyl species, focusing on NO oxidation.

Main Results:

  • A diiron dinitrosyl species ({FeNO}2) and a mononitrosyl diiron species (Fe{FeNO}) were formed and characterized.
  • Oxidation of the diiron dinitrosyl species ({FeNO}2) yielded nitrite with a high efficiency of 71%.
  • This demonstrates the first successful synthetic replication of Mka-HLP's NO oxidase activity.

Conclusions:

  • The synthesized diiron complex effectively models the NO oxidase function of Mka-HLP.
  • The study suggests the involvement of {FeNO}2/{FeNO} species as intermediates in this NO oxidation process.
  • This work provides valuable insights into bacterial strategies for NO detoxification and immune evasion.