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Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

19.7K
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...
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Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.8K
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...
4.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.1K
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...
5.1K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
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,...
2.8K
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

5.0K
Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
5.0K

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Measuring Magnetically-Tuned Ferroelectric Polarization in Liquid Crystals
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Reversible Double Nucleophilic Substitution Reaction inside Single-Crystal MOF Tuned Remarkable Magnetic Behavior.

Hai-Yun Ren1, Xian-Ming Zhang1

  • 1School of Chemistry & Material Science , Shanxi Normal University , Linfen , Shanxi 041004 , China.

Inorganic Chemistry
|June 7, 2018
PubMed
Summary

This study details a novel 3D coordination network that enables reversible single-crystal reactions. This process allows for tunable magnetism, shifting from antiferromagnetism to ferromagnetism.

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Area of Science:

  • Materials Science
  • Crystallography
  • Magnetism

Background:

  • Single-crystal chemical reactions offer high selectivity but present significant challenges.
  • Coordination networks are versatile materials with tunable properties.

Purpose of the Study:

  • To synthesize a novel 3D coordination network based on octahedral cobalt-oxygen chains.
  • To investigate the possibility of performing reversible nucleophilic substitution reactions within a single crystal.
  • To explore the magnetic properties and tunability of the resulting material.

Main Methods:

  • Synthesis of a 3D coordination network with sqc3868 topology.
  • Single-crystal X-ray diffraction to determine structural changes.
  • UV-vis, XPS, EPR, and XANES spectroscopy to analyze electronic structure.
  • Magnetic measurements to study magnetic transitions.

Main Results:

  • A reversible double nucleophilic substitution occurred within the single crystal, transforming the sqc3868 topology to a related frl network.
  • The transformation involved encapsulated dimethylformamide (DMF) molecules.
  • Magnetic properties tuned from antiferromagnetism to ferromagnetism.
  • Spectroscopic analysis indicated that cobalt centers remained primarily in the divalent state with minimal electronic structure changes.

Conclusions:

  • The observed magnetic tunability is attributed to minor changes in the local geometry of cobalt atoms, which possess large anisotropy.
  • This work demonstrates a strategy for achieving controlled chemical transformations and magnetic tuning within single crystals.