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Related Concept Videos

Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
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Carbocations

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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...
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Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

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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...
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
5.1K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Updated: May 16, 2025

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Formation Of Gold-Astatine Bonds in N-Heterocyclic Carbene Complexes.

Mathilde Ligeour1, Sébastien G Guillet1, Clémence Maingueneau1

  • 1CRCI2NA, Nantes Université, Inserm, CNRS, Université d'Angers, 8 quai Moncousu, Nantes Cedex, 44007, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 11, 2025
PubMed
Summary

Researchers explored gold complexes for improved radiopharmaceuticals. Gold(I) N-heterocyclic carbene complexes show promise for stable astatine (At) radiolabeling, offering a superior alternative to current methods for cancer therapy applications.

Keywords:
astatinegoldn‐heterocyclic Carbeneradiochemistryradiolabeling

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Area of Science:

  • Radiopharmaceutical Chemistry
  • Inorganic Chemistry
  • Computational Chemistry

Background:

  • Current 211At-labeled radiopharmaceuticals suffer from unstable astatoaryl bonds.
  • Astatine (At) is a promising radioisotope for targeted alpha therapy in cancer treatment.
  • Novel coordination strategies are needed to enhance the stability of 211At radiotracers.

Purpose of the Study:

  • To investigate the coordination of astatine (At) with metal-N-heterocyclic carbene (NHC) complexes.
  • To explore alternatives to the unstable astatoaryl bond in 211At-labeled radiopharmaceuticals.
  • To evaluate the potential of gold(I) complexes for stable 211At radiolabeling.

Main Methods:

  • Relativistic Density Functional Theory (DFT) calculations were employed to assess metal-astatine bond strengths and metal preferences.
  • Gold(I) complexes, specifically [AuCl(IPr)] and [AuCl(IAd)], were synthesized and radiolabeled using iodine-125 and astatine-211 via halide exchange.
  • Radiochemical yields and the stability of the radiolabeled complex [Au211At(IPr)] in phosphate-buffered saline were evaluated.

Main Results:

  • Relativistic DFT calculations indicated that gold(I) forms stronger bonds with astatine compared to rhodium(I) and iridium(I).
  • Electron-withdrawing N-heterocyclic carbene (NHC) ligands enhanced the stability of the metal-astatine bond.
  • [Au211At(IPr)] demonstrated excellent stability in phosphate-buffered saline, retaining 96% of the radioactivity after two half-lives.

Conclusions:

  • Gold(I) complexes, particularly those with electron-withdrawing NHC ligands, offer a promising platform for developing stable 211At-labeled radiopharmaceuticals.
  • The enhanced stability of the gold-astatine bond presents a viable alternative to the astatoaryl linkage.
  • The excellent stability and radiolabeling efficiency of [Au211At(IPr)] encourage further development for cancer-targeting applications.