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Related Concept Videos

Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Functional Groups02:45

Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...
Introduction to Functional Groups02:08

Introduction to Functional Groups


Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of common functional groups
The table below summarizes some of the major functional groups in organic chemistry. (The...
Overview of Advanced Functional Groups02:22

Overview of Advanced Functional Groups


Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of Advanced Functional Groups
The table below summarizes some of the major functional groups in organic chemistry.
Functional Groups02:45

Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...
Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Amine-chelated aryllithium reagents--structure and dynamics.

H J Reich1, W S Goldenberg, B O Gudmundsson

  • 1Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.

Journal of the American Chemical Society
|August 17, 2001
PubMed
Summary
This summary is machine-generated.

Five-membered-ring amine chelated aryllithium reagents exhibit strong chelation and form stable dimers in ethereal solvents. These dimers show unique chelation isomers and enhanced thermodynamic and kinetic stability compared to model systems.

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Published on: April 26, 2024

Area of Science:

  • Organometallic Chemistry
  • Solution-state structural analysis
  • Lithium chemistry

Background:

  • Aryllithium reagents are crucial in organic synthesis.
  • Understanding their aggregation and solvation is key to controlling reactivity.
  • Chelation by amine groups significantly influences lithium reagent behavior.

Purpose of the Study:

  • To elucidate the solution structures of five-membered-ring amine chelated aryllithium reagents.
  • To investigate the impact of various ethereal solvents and cosolvents (TMEDA, PMDTA, HMPA) on these structures.
  • To compare the stability and aggregation behavior with model aryllithium systems.

Main Methods:

  • Multinuclear NMR spectroscopy (isotopically enriched in 6Li and 15N) was employed.
  • Dynamic NMR studies were used to determine interconversion rates and activation energies.
  • X-ray crystallography provided solid-state structural confirmation.

Main Results:

  • All studied reagents are strongly chelated and form stable dimers in THF-rich solvents.
  • Three distinct chelation isomers (A, B, C) of the dimers were identified and characterized.
  • These dimers exhibit greater thermodynamic and kinetic stability than model aryllithium compounds.
  • The o-methoxy analogue (4) shows reduced dimerization due to steric hindrance but can form triple ions with HMPA.

Conclusions:

  • The amine chelation strongly stabilizes dimeric aryllithium species.
  • Dynamic processes involving amine decoordination and ring rotation govern isomer interconversion.
  • Chelated aryllithium dimers represent robust and stable organometallic structures.