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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Aromatic Hydrocarbon Anions: Structural Overview01:18

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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.
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Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...
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sp3d and sp3d 2 Hybridization
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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The hexacyanodiborane(6) dianion [B2(CN)6](2-).

Johannes Landmann1, Jan A P Sprenger1, Michael Hailmann1

  • 1Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany).

Angewandte Chemie (International Ed. in English)
|July 30, 2015
PubMed
Summary

A new, robust hexacyanodiborane(6) dianion, [B2(CN)6](2-), has been synthesized. This air-stable boron compound exhibits remarkable resistance to heat, water, and hydrogen fluoride, opening avenues for material applications.

Keywords:
boratesboroncyanoboratesdiborane(6)

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Area of Science:

  • Inorganic Chemistry
  • Boron Chemistry
  • Organometallic Chemistry

Background:

  • Diborane(6) dianions with carbon-boron bonds are typically highly reactive and rare.
  • Diborane(6) derivatives are fundamental electron-precise boron compounds with potential material applications.

Purpose of the Study:

  • To synthesize and characterize a chemically robust homoleptic hexacyanodiborane(6) dianion.
  • To investigate the stability and synthetic accessibility of the [B2(CN)6](2-) dianion.

Main Methods:

  • Synthesis of the [B2(CN)6](2-) dianion via three distinct routes.
  • Characterization of the dianion's stability towards air, water, hydrogen fluoride, and thermal decomposition.
  • Investigation of reaction mechanisms, including SN2 pathways.

Main Results:

  • The homoleptic hexacyanodiborane(6) dianion, [B2(CN)6](2-), was successfully synthesized and found to be chemically robust.
  • [B2(CN)6](2-) is air-stable and resistant to boiling water and anhydrous hydrogen fluoride.
  • Salts of [B2(CN)6](2-) exhibit high thermal stability, with decomposition of (H3O)2[B2(CN)6] starting above 200°C.
  • The dianion is accessible through reactions involving B(CN)3(2-), [BF(CN)3](-), and oxidants/reductants, or via reaction with [BHal(CN)3](-).

Conclusions:

  • The hexacyanodiborane(6) dianion represents a significant advancement in boron chemistry due to its exceptional stability.
  • The reported synthetic routes provide accessible methods for preparing this robust boron compound.
  • The stability profile of [B2(CN)6](2-) suggests potential for its use in advanced material applications.