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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
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Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
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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...
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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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Controlling and predicting alkyl-onium electronic structure.

Frances K Towers Tompkins1, Lewis G Parker1, Richard M Fogarty2

  • 1Department of Chemistry, University of Reading, UK. k.r.j.lovelock@reading.ac.uk.

Chemical Communications (Cambridge, England)
|September 9, 2024
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Summary
This summary is machine-generated.

Researchers tuned onium cation electronic structure using alkyl chains and the central atom. Methyl versus longer chains are key for optimizing cations for catalysis and biocides.

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Area of Science:

  • Materials Science
  • Computational Chemistry

Background:

  • Onium cations are versatile chemical species.
  • Tuning their electronic properties is crucial for targeted applications.

Purpose of the Study:

  • To investigate the tunability of fully alkylated onium cation electronic structure.
  • To identify key structural factors influencing these properties.

Main Methods:

  • X-ray photoelectron spectroscopy (XPS) for electronic structure analysis.
  • Ab initio quantum mechanical calculations for theoretical validation.

Main Results:

  • Electronic structure is tunable via both alkyl chain length and the central onium atom.
  • The choice between methyl and longer alkyl chains significantly impacts the central atom's electronic state.

Conclusions:

  • The electronic structure of onium cations can be precisely engineered.
  • This tunability enables the selection of optimal cations for diverse applications, including catalysis and biocides.