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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.1K
Diazonium Group Substitution: –OH and –H01:19

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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.
2.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
SN2 Reaction: Kinetics02:14

SN2 Reaction: Kinetics

8.8K
Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
8.8K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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2.0K
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...
2.0K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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4.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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2-Substituted vs 2,9-Disubstituted Phenanthroline-NiII-halides: Speciation Control and Structural Elucidation in

Ana Mateos-Calbet1, Markus Leutzsch1, Maurice van Gastel1

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Nickel(II) halide complexes with phenanthroline ligands exhibit distinct speciation. Dibromido complexes form monomers in solution, while diiodido complexes remain monomeric in solid and solution states.

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Area of Science:

  • Coordination chemistry
  • Organometallic chemistry
  • Materials science

Background:

  • Phenanthroline ligands are crucial in coordination chemistry.
  • Nickel(II) halide complexes exhibit diverse structural and electronic properties.
  • Understanding speciation is key for catalyst design and materials development.

Purpose of the Study:

  • To investigate the structural and solution behavior of 2,9-disubstituted and 2-monosubstituted phenanthroline Ni(II)-dibromido and diiodido complexes.
  • To elucidate the influence of ligand substitution and halide identity on complex speciation.
  • To correlate solid-state structures with solution behavior.

Main Methods:

  • Single-crystal X-ray diffraction (SC-XRD) for solid-state structure determination.
  • SQUID magnetometry for magnetic property analysis.
  • UV-vis-NIR spectroscopy and Diffusion Ordered Spectroscopy (DOSY) NMR for solution speciation studies.

Main Results:

  • Nickel(II) dibromido complexes, regardless of phenanthroline substitution, form monomeric species in THF and CDCl3 solutions.
  • Nickel(II) diiodido complexes remain monomeric in both solid state and solution, irrespective of ligand substitution.
  • Divergent speciation was observed between solid-state and DMF solution for Ni(II)-dibromido complexes.

Conclusions:

  • Phenanthroline ligand substitution and halide identity significantly influence nickel(II) complex speciation.
  • Nickel(II) diiodido complexes offer robust monomeric structures across different phases.
  • The findings provide insights into the design of nickel-based coordination compounds with predictable solution behavior.