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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...
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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 an...
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Negative hyperconjugation in phosphorus stabilized carbanions.

Tom Leyssens1, Daniel Peeters

  • 1Laboratoire de Chimie Quantique, Université Catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium. t.leyssens@chim.ucl.ac.be

The Journal of Organic Chemistry
|March 1, 2008
PubMed
Summary

Phosphorus-stabilized carbanions exhibit electronic delocalization, confirmed by the electronic Fukui function and NBO analyses. This interaction explains their unique energetic, electronic, and structural properties, including bond lengths and angles.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Phosphorus-stabilized carbanions are important intermediates in organic synthesis.
  • Understanding their electronic structure is crucial for predicting reactivity.
  • Previous studies have suggested electronic interactions involving phosphorus functional groups.

Purpose of the Study:

  • To provide electronic evidence for back-bonding in phosphorus-stabilized carbanions.
  • To investigate the energetic, electronic, and structural consequences of negative hyperconjugation.
  • To elucidate the electronic role of phosphorus-containing functional groups.

Main Methods:

  • Utilized the electronic Fukui function for qualitative electronic analysis.
  • Employed Natural Bond Orbital (NBO) analyses to study electronic delocalization.
  • Compared electronic and structural properties of anionic and neutral compounds.

Main Results:

  • Confirmed back-bonding from the carbon lone pair to sigma* P-Y and P-O orbitals.
  • Observed significant energetic stabilization due to lone pair delocalization into antibonding orbitals.
  • Identified structural changes: shorter P-C bonds, longer P-Y/P-O bonds, and wider Y-P-Y angles in carbanions.

Conclusions:

  • Negative hyperconjugation is a key interaction in phosphorus-stabilized carbanions.
  • Electronic delocalization explains the observed energetic and structural features.
  • Phosphorus functional groups act as sigma donors and pi acceptors.