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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Substitution matters: isolating phosphorus diiminopyridine complexes.

Caleb D Martin1, Paul J Ragogna

  • 1Department of Chemistry, The University of Western Ontario, London, ON, Canada.

Dalton Transactions (Cambridge, England : 2003)
|October 11, 2011
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel phosphorus(I) cations by reacting phosphorus triiodide with specific diiminopyridine ligands. Ligand substitution significantly impacts reaction outcomes, highlighting the importance of molecular structure in phosphorus chemistry.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods
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Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods

Published on: October 6, 2023

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Published on: November 22, 2016

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods
07:20

Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods

Published on: October 6, 2023

Area of Science:

  • Coordination Chemistry
  • Organophosphorus Chemistry
  • Inorganic Synthesis

Background:

  • Diiminopyridine ligands are versatile chelating agents in coordination chemistry.
  • The synthesis and reactivity of low-valent phosphorus complexes remain an active area of research.
  • Understanding substituent effects is crucial for controlling reactivity and product formation.

Purpose of the Study:

  • To explore the direct reaction of phosphorus triiodide (PI(3)) with substituted diiminopyridine ligands.
  • To investigate the influence of α-carbon substituents on the diiminopyridine ring on reaction outcomes.
  • To synthesize and characterize novel phosphorus(I) diiminopyridine complexes.

Main Methods:

  • Direct reaction of PI(3) with diiminopyridine ligands bearing -H, -CH(3), and -C(6)H(5) substituents.
  • Anion exchange reactions using the B(12)Cl(12)(2-) dianion.
  • Reactions of phosphorus trichloride (PCl(3)) and phosphorus tribromide (PBr(3)) with diiminopyridine ligands.
  • Utilizing a halide trap in reactions involving PBr(3).

Main Results:

  • Direct reaction of PI(3) with -H and -C(6)H(5) substituted ligands yielded N,N',N''-chelated P(I) cations.
  • Reaction with the -CH(3) substituted ligand resulted in a complex product mixture, indicating substituent sensitivity.
  • The iodide counteranion (I(3)(-)) was successfully exchanged for the more stable B(12)Cl(12)(2-) dianion.
  • Reactions with PCl(3) and PBr(3) generally led to unreactive mixtures or no reaction, except for PBr(3) with the -H derivative under specific conditions.
  • The synthesis of the first reported phosphorus diiminopyridine complexes was achieved.

Conclusions:

  • The α-carbon substitution on diiminopyridine ligands critically influences the outcome of reactions with PI(3).
  • Phosphorus(I) cations can be synthesized and stabilized within diiminopyridine coordination spheres.
  • The developed synthetic routes provide access to a new class of organophosphorus coordination compounds.