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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.
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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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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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The 9-Borataphenanthrene Anion.

Tyler A Bartholome1, Aishvaryadeep Kaur2, David J D Wilson2

  • 1Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, TX, 76798-7343, USA.

Angewandte Chemie (International Ed. in English)
|April 3, 2020
PubMed
Summary
This summary is machine-generated.

The novel 9-borataphenanthrene anion, readily synthesized, exhibits versatile reactivity including alkylation and hydroboration. This organoboron compound demonstrates potential as a ligand in coordination chemistry.

Keywords:
borataalkeneboratabenzeneboronheterocycleshydroboration

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Area of Science:

  • Organometallic Chemistry
  • Boron Chemistry
  • Ligand Design

Background:

  • Exploration of novel organoboron compounds is crucial for advancing synthetic chemistry.
  • Understanding the reactivity and coordination behavior of boron-containing heterocycles is an active research area.

Purpose of the Study:

  • To synthesize and investigate the reactivity of the 9-borataphenanthrene anion.
  • To explore the potential of this anion as a versatile ligand in coordination chemistry.

Main Methods:

  • Deprotonation of 9,10-dihydro-9-boraphenanthrene to access the anion.
  • Reactivity studies including alkylation and hydroboration.
  • Coordination studies with transition metals (chromium and gold).
  • Computational analysis using nucleus-independent chemical shift (NICS) for aromaticity.

Main Results:

  • The 9-borataphenanthrene anion was successfully synthesized.
  • Alkylation occurred at the carbon adjacent to boron, and hydroboration across the B=C bond was observed.
  • The anion coordinated to chromium (η6) and gold (η2), showcasing its diverse ligand capabilities.

Conclusions:

  • The 9-borataphenanthrene anion displays rich and versatile reactivity.
  • Its ability to coordinate to different transition metals highlights its potential as a tunable ligand.
  • Computational results support the observed reactivity and confirm the aromatic nature of the system.