Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Nucleophiles02:30

Nucleophiles

16.6K
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...
16.6K
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

19.5K
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...
19.5K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.7K
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...
4.7K
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

8.2K
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...
8.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.7K
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...
2.7K
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

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Diastereoselective and Chemically Reversible C-C Bond Formation Mediated by an (N-heterocyclic)boryloxy Aluminyl Compound.

Journal of the American Chemical Society·2026
Same author

Cyaphide generation at an aluminium(i) center: a useful precursor for phosphorus-containing heterocycles.

Chemical science·2026
Same author

Xanthene-to-fluorene skeletal editing <i>via</i> oxygen deletion mediated by boron and aluminium radicals.

Chemical science·2026
Same author

Cyaphido Complexes of the Rare-Earth Metals and Their Tetramerization.

Journal of the American Chemical Society·2026
Same author

Homo- and Heteroleptic Silylstannylenes: Synthesis, Structure and Use as Precursors to Bimetallic Compounds.

Organometallics·2026
Same author

Alumanyl silanides as multifunctional reagents for olefin cycloaddition, CO hydrosilylation, and reductive CO coupling.

Chemical science·2026
Same journal

Setting a direction for molecular motors.

Nature chemistry·2026
Same journal

Driving movement in the field of molecular machines.

Nature chemistry·2026
Same journal

First ladies of chemistry.

Nature chemistry·2026
Same journal

How isoprene connects plants to global climate.

Nature chemistry·2026
Same journal

One-dimensional carbon chains free of end-capping groups.

Nature chemistry·2026
Same journal

Covalency control of photomagnetic relaxation in a manganese(II) photoswitch.

Nature chemistry·2026
See all related articles

Related Experiment Video

Updated: Jan 30, 2026

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- &#181;CP and Sequential Nucleophilic Substitution
08:23

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- µCP and Sequential Nucleophilic Substitution

Published on: October 31, 2014

10.9K

A nucleophilic gold complex.

Jamie Hicks1, Akseli Mansikkamäki2, Petra Vasko1,2

  • 1Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.

Nature Chemistry
|January 22, 2019
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel gold complex, (NON)AlAuPtBu3, demonstrating that gold can act as a nucleophile in solution. This discovery opens new avenues for gold chemistry by enabling the formation of gold-carbon bonds.

More Related Videos

Gold Nanoparticle Synthesis
13:42

Gold Nanoparticle Synthesis

Published on: July 10, 2021

15.9K
Synthesis and Characterization of Amphiphilic Gold Nanoparticles
10:09

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

Published on: July 2, 2019

18.2K

Related Experiment Videos

Last Updated: Jan 30, 2026

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- &#181;CP and Sequential Nucleophilic Substitution
08:23

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- µCP and Sequential Nucleophilic Substitution

Published on: October 31, 2014

10.9K
Gold Nanoparticle Synthesis
13:42

Gold Nanoparticle Synthesis

Published on: July 10, 2021

15.9K
Synthesis and Characterization of Amphiphilic Gold Nanoparticles
10:09

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

Published on: July 2, 2019

18.2K

Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Gold Chemistry

Background:

  • Solid-state auride salts (Au-) are stable with alkali metals but their nucleophilicity in solution is unconfirmed due to instability.
  • Electron-rich gold species are theoretically expected to exhibit nucleophilic behavior, similar to halides.

Purpose of the Study:

  • To synthesize and characterize a novel gold complex with a polarized Au-Al bond.
  • To experimentally verify the nucleophilic character of a gold complex in solution.
  • To explore the reactivity of this gold complex in insertion reactions.

Main Methods:

  • Synthesis of the two-coordinate gold complex (NON)AlAuPtBu3 via reaction of a potassium aluminyl compound with a gold(I) iodide.
  • Characterization using computational studies, including Quantum Theory of Atoms in Molecules (QTAIM) charge analysis.
  • Experimental investigation of the complex's reactivity with electrophiles like diisopropylcarbodiimide and carbon dioxide.

Main Results:

  • Successful synthesis of the gold complex (NON)AlAuPtBu3 featuring a polarized Auδ--Alδ+ bond.
  • Computational analysis indicated a significant negative charge on gold (Au: -0.82), consistent with relative electronegativities.
  • The complex demonstrated nucleophilic behavior, reacting with diisopropylcarbodiimide and CO2 to form Au-C bonded insertion products.

Conclusions:

  • The study presents the first experimental evidence of a gold complex acting as a nucleophilic gold source in solution.
  • The synthesized complex provides a stable platform for exploring the nucleophilicity of gold.
  • This work expands the known reactivity of gold complexes and offers new synthetic pathways for gold-carbon bond formation.