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

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

You might also read

Related Articles

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

Sort by
Same author

Ligand-Controlled Redox and Photophysical Properties in Photoluminescent Tris-Heteroleptic Ru(II) Pyridyl-Phosphonium Ylide Complexes.

Inorganic chemistry·2026
Same author

State-of-the-Art and Synthetic Challenges for Hydrosilane Production.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Bipyridyl Ruthenium Complexes Featuring P-Ylide Ligands: A Comparative Study of Their Redox and Photophysical Properties.

Inorganic chemistry·2025
Same author

Catalytic olefin hydrosilylation with an original bis(iminophosphorane)phosphine NPN Co<sup>II</sup> complex.

Dalton transactions (Cambridge, England : 2003)·2025
Same author

Experimental Evaluation of the Hydricity of Hydrosilanes.

Inorganic chemistry·2025
Same author

Scandium-Catalyzed Highly Selective Deoxygenation of Alcohols by Using Hydrosilanes as Reductants.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025

Related Experiment Video

Updated: Jul 6, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

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

Published on: November 22, 2016

Bis-phosphorus stabilised carbene complexes.

Thibault Cantat1, Nicolas Mézailles, Audrey Auffrant

  • 1Ecole Polytechnique, CNRS, Laboratoire Hétéroéléments et Coordination, Route de Saclay, F-91128, Palaiseau, France.

Dalton Transactions (Cambridge, England : 2003)
|April 3, 2008
PubMed
Summary

The electronic properties and reactivity of metal-carbene complexes are tuned by phosphorus substituents. Varying phosphorus coordination influences carbene center stabilization, leading to diverse reactivity in transition metal and lanthanide complexes.

More Related Videos

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Related Experiment Videos

Last Updated: Jul 6, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

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

Published on: November 22, 2016

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Main Group Chemistry

Background:

  • Carbene centers in metal complexes are stabilized by metal or carbon substituents.
  • The balance of these effects dictates M=C bond character and complex reactivity.
  • Phosphorus substituents offer tunable electronic properties based on their coordination.

Purpose of the Study:

  • To investigate the impact of vicinal phosphorus substituents on carbene center stabilization.
  • To explore how different phosphorus coordination states (sigma(3)-P vs. sigma(4)-P) affect electronic properties.
  • To understand the resulting electrophilic or nucleophilic reactivity of PCP carbene complexes.

Main Methods:

  • Theoretical analysis of electronic interactions between phosphorus substituents and the carbene center.
  • Discussion of relevant literature examples involving PCP carbene complexes.
  • Consideration of complexes with early and late transition metals, and lanthanides.

Main Results:

  • A sigma(3)-P atom can destabilize the carbene p(pi) orbital via lone pair interaction.
  • A sigma(4)-P group can delocalize electron density into the carbene p(pi) orbital through negative hyperconjugation.
  • PCP carbene complexes exhibit tunable electronic properties and reactivity.

Conclusions:

  • The coordination state of vicinal phosphorus groups critically influences the electronic nature of PCP carbene complexes.
  • This electronic modulation allows for control over whether the complex behaves as an electrophile or nucleophile.
  • The findings are applicable to a broad range of metal centers, including transition metals and lanthanides.