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Related Concept Videos

Carbocations02:10

Carbocations

11.3K
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...
11.3K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

2.4K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Ionic Bonding and Electron Transfer02:48

Ionic Bonding and Electron Transfer

46.6K
Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions. 
46.6K
Electrophiles02:28

Electrophiles

9.8K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
9.8K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.1K
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.
8.1K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

2.4K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
2.4K

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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How can a carbene be active in an ionic liquid?

Martin Thomas1, Martin Brehm, Oldamur Hollóczki

  • 1Mulliken Center for Theoretical Chemistry, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4,D-53115 Bonn (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 31, 2013
PubMed
Summary
This summary is machine-generated.

N-heterocyclic carbenes are highly reactive in ionic liquids because acetate ions block typical stabilization sites. A novel C⋅⋅⋅H-C hydrogen bond forms with the methyl group, offering new ways to tune solvent interactions.

Keywords:
N-heterocyclic carbeneshydrogen bondsionic liquidsreactivitysolvation

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Area of Science:

  • Chemistry
  • Materials Science

Background:

  • N-heterocyclic carbenes (NHCs) are vital catalysts.
  • Ionic liquids (ILs) are versatile solvents.
  • Understanding NHC-IL interactions is key for catalysis.

Purpose of the Study:

  • Investigate the solvation of 1-ethyl-3-methylimidazole-2-ylidene in 1-ethyl-3-methylimidazolium acetate.
  • Elucidate the interactions between NHCs and ILs.

Main Methods:

  • Ab initio molecular dynamics simulations were employed.
  • The study focused on the specific carbene and ionic liquid system.

Main Results:

  • Acetate ions occupy the acidic ring hydrogens of the imidazolium cation, preventing carbene stabilization.
  • A novel C⋅⋅⋅H-C hydrogen bond interaction was observed between the carbene and the methyl group of the imidazolium cation.
  • This interaction is weaker than typical hydrogen bonds but influences carbene reactivity.

Conclusions:

  • The absence of stabilization by ring hydrogens explains the high reactivity of carbenes in acetate-based ILs.
  • The novel C⋅⋅⋅H-C interaction provides a new perspective on solute-solvent interactions in ILs.
  • This finding offers a new site for tuning the ionic liquid environment for dissolved species.