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Related Concept Videos

Nucleophiles02:30

Nucleophiles

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The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as...
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Nucleophilic Substitution Reactions02:34

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

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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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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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

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The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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An Anionic Aluminium Nucleophile.

Alexander Hinz1, Frank Breher1

  • 1Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry, Engesserstr. 15, 76131, Karlsruhe, Germany.

Angewandte Chemie (International Ed. in English)
|June 15, 2018
PubMed
Summary
This summary is machine-generated.

Researchers isolated the first stable anionic aluminium nucleophile, a highly reactive aluminyl compound. This discovery advances main group chemistry, enabling new reactions like oxidative addition and metathesis.

Keywords:
aluminiumlow-valent speciesmain group chemistrynucleophilesumpolung

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Main Group Chemistry

Background:

  • Stable anionic species are crucial for advancing chemical synthesis.
  • Aluminium chemistry has historically been limited by the instability of anionic forms.
  • Previous research focused on Lewis acidic aluminium compounds.

Purpose of the Study:

  • To synthesize and characterize the first stable anionic aluminium nucleophile.
  • To investigate the reactivity of this novel aluminyl compound.
  • To explore new synthetic pathways in main group chemistry.

Main Methods:

  • Isolation and characterization of the anionic aluminium compound.
  • Experimental studies on its reactivity in various chemical transformations.
  • Spectroscopic and crystallographic analyses.

Main Results:

  • Successful isolation of the first stable anionic aluminium nucleophile (aluminyl compound).
  • Demonstrated high reactivity in metathesis reactions.
  • Exhibited significant activity in the oxidative addition of substrates like dihydrogen and benzene.

Conclusions:

  • The discovery of a stable anionic aluminium nucleophile opens new frontiers in main group chemistry.
  • This compound's reactivity enables novel synthetic transformations.
  • Provides a new platform for exploring aluminium's role in catalysis and synthesis.