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...
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...
Complexation Equilibria: Overview01:23

Complexation Equilibria: Overview

Complexation reactions take place when dative or coordinate covalent bonds form between metal ions and ligands. The compounds formed in these reactions are called coordination compounds. The number of bonds formed between the metal ion and the ligands is called its coordination number. Generally, most metal ions in an aqueous solution are solvated by water molecules and thus exist as aqua complexes.
The equilibrium constant of the complexation reaction is represented as the formation constant...
Ladder Diagrams: Complexation Equilibria01:07

Ladder Diagrams: Complexation Equilibria

Ladder diagrams are useful for evaluating equilibria involving metal-ligand complexes. The vertical scale of the ladder diagram represents the concentration of unreacted or free ligand, pL. The horizontal lines on the scale depict the log of stepwise formation constants for metal-ligand complexes and indicate the dominant species in all the regions.
The formation constant, K1, for the formation of Cd(NH3)2+ complex from cadmium and ammonia is 3.55 × 102. Log K1 (i.e. pNH3) is 2.55, and...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

You might also read

Related Articles

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

Sort by
Same author

Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes.

The Journal of organic chemistry·2020
Same author

Polar molecules catalyze CO insertion into metal-alkyl bonds through the displacement of an agostic C-H bond.

Proceedings of the National Academy of Sciences of the United States of America·2019
Same author

Selective Dehydrogenative Coupling of Ethylene to Butadiene via an Iridacyclopentane Complex.

Journal of the American Chemical Society·2018
Same author

Experimental and computational study of alkane dehydrogenation catalyzed by a carbazolide-based rhodium PNP pincer complex.

Chemical science·2017
Same author

Catalytic Dehydrogenative C-C Coupling by a Pincer-Ligated Iridium Complex.

Journal of the American Chemical Society·2017
Same author

β-Hydride Elimination and C-H Activation by an Iridium Acetate Complex, Catalyzed by Lewis Acids. Alkane Dehydrogenation Cocatalyzed by Lewis Acids and [2,6-Bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl]iridium.

Journal of the American Chemical Society·2017
Same journal

Gas-Responsive Metal-Organic Frameworks for Adaptive Thermal Energy Storage with Tunable Charge-Discharge Temperatures.

Journal of the American Chemical Society·2026
Same journal

Engineering a Thiamine-Dependent Benzoylformate Decarboxylase for Stereodivergent Radical C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Bond Formation.

Journal of the American Chemical Society·2026
Same journal

Accelerated Directional Proton-Coupled Electron Transfer Enabled by Intrinsic Dipole Field in Biomimetic α-Helical Structure.

Journal of the American Chemical Society·2026
Same journal

Alternating Current-Driven Hydrogen Isotope Labeling of Aliphatic Amines Using 1,3-Propanedithiol as an Efficient Hydrogen Atom Transfer Reagent.

Journal of the American Chemical Society·2026
Same journal

Two-Dimensional van der Waals Polar Metal MoOBr<sub>2</sub>.

Journal of the American Chemical Society·2026
Same journal

Negatively Curved Chiral Bilayer Nanographene.

Journal of the American Chemical Society·2026
See all related articles

Related Experiment Video

Updated: Jun 10, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

A carbene-carbene complex equilibrium.

Robert A Moss1, Lei Wang, Christina M Odorisio

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu

Journal of the American Chemical Society
|August 5, 2010
PubMed
Summary
This summary is machine-generated.

Phenylchlorocarbene forms stable pi-type complexes with 1,3,5-trimethoxybenzene. These carbene complexes exist in equilibrium with the carbene, with measured thermodynamic parameters indicating stability.

More Related Videos

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Related Experiment Videos

Last Updated: Jun 10, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Supramolecular Chemistry

Background:

  • Carbenes are highly reactive intermediates crucial in organic synthesis.
  • Understanding carbene interactions with aromatic systems is key to controlling reactivity.
  • Phenylchlorodiazirine serves as a precursor for generating phenylchlorocarbene.

Purpose of the Study:

  • To investigate the formation and stability of pi-type complexes between phenylchlorocarbene and 1,3,5-trimethoxybenzene.
  • To quantify the equilibrium and thermodynamic parameters governing this carbene-arene interaction.

Main Methods:

  • Generation of phenylchlorocarbene via laser flash photolysis of phenylchlorodiazirine.
  • Spectroscopic characterization (UV-vis) of carbene-arene complexes.
  • Computational analysis to support experimental findings.
  • Determination of equilibrium constants and thermodynamic parameters through temperature-dependent studies.

Main Results:

  • Highly stable pi-type complexes were formed between phenylchlorocarbene and 1,3,5-trimethoxybenzene in pentane.
  • The carbene and its complexes were found to be in equilibrium.
  • The equilibrium constant (K = 1264 M⁻¹) and thermodynamic parameters (ΔH° = -7.1 kcal/mol, ΔS° = -10.2 eu, ΔG° = -4.1 kcal/mol) were determined at 294 K.

Conclusions:

  • Phenylchlorocarbene readily forms stable pi-type complexes with electron-rich aromatic compounds like 1,3,5-trimethoxybenzene.
  • The equilibrium and thermodynamic data provide quantitative insights into the stability and nature of these carbene-arene interactions.
  • This study highlights the potential for stabilizing reactive carbene species through complexation.