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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Prochirality02:05

Prochirality

4.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
13.9K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

14.0K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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Laterally Distorted 1,2-Dibora-4-gallatacyclopentane Anion.

A Wahid Mesbah1, Meisam Soleimani1, Fatemeh Akbari Lasboo1

  • 1Chemistry & Chemical Engineering Research Center of Iran, 14968-13151 Tehran, Iran.

Inorganic Chemistry
|December 18, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel 1,2-dibora-4-gallatacyclopentane anion. This unique boron-gallium compound exhibits a distorted, nonplanar ring structure due to electronic interactions.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Cyclopentane derivatives are fundamental in organic chemistry.
  • Boron and gallium compounds offer unique electronic and structural properties.
  • Understanding heterocycles containing main group elements is crucial for novel material development.

Purpose of the Study:

  • To synthesize and characterize a novel five-membered ring containing boron and gallium.
  • To investigate the structural and electronic properties of the 1,2-dibora-4-gallatacyclopentane anion.
  • To explore the influence of heteroatoms on ring geometry compared to carbon-based analogues.

Main Methods:

  • Synthesis via reaction of dilithium salt of 2,3-diboratabutadiene with Ga2I3.
  • Characterization using multinuclear NMR spectroscopy (11B, 1H, 13C).
  • Structural analysis via single-crystal X-ray diffraction.

Main Results:

  • Successful synthesis of the 1,2-dibora-4-gallatacyclopentane anion.
  • Determination of a distorted, nonplanar five-membered ring structure.
  • Observed Ga-C-B angles (~95.1°) significantly smaller than cyclopentane (104.4°).
  • Torsion angle C-B-B-C (60.3°) is substantially larger than in cyclopentane (14.4°).
  • Structural distortion attributed to σ(Ga-C) bond and boron p-orbital interactions.

Conclusions:

  • The synthesized 1,2-dibora-4-gallatacyclopentane anion represents a novel heterocyclic compound.
  • Electronic interactions between gallium-carbon bonds and boron atoms dictate the nonplanar ring geometry.
  • This study expands the understanding of main group element-containing heterocycles and their unique structural features.