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Related Concept Videos

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.
Removing one hydrogen from the intervening CH2 group...
3.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

10.4K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
10.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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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Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

5.2K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
5.2K
Valence Bond Theory02:42

Valence Bond Theory

9.8K
Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Metalla-phenalene complexes: synthesis, structure and aromaticity.

Yue Sun1, Yan Zhou2, Wei Bai1

  • 1State Key Laboratory of Fine Chemicals, Department of Chemistry, School of Chemical Engineering, Dalian University of Technology, Liaoning 116024, P. R. China. baiwei@dlut.edu.cn.

Chemical Communications (Cambridge, England)
|December 13, 2021
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel rhena-phenalene complexes, revealing unique aromaticity. These metal-aromatic compounds exhibit Hückel, sigma, and pseudo π anti-aromaticity, with DFT confirming the naphthyl ring

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Structure and Coordination Determination of Peptide-metal Complexes Using 1D and 2D 1H NMR
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Area of Science:

  • Organometallic chemistry
  • Aromaticity studies
  • Coordination chemistry

Background:

  • Metallaaromatics exhibit diverse aromatic behaviors.
  • Understanding aromaticity in metal-containing systems is crucial.

Purpose of the Study:

  • To synthesize and structurally characterize the first rhena-phenalene complexes.
  • To investigate the aromatic properties of these novel compounds.

Main Methods:

  • Synthesis of novel organometallic compounds.
  • X-ray crystallography for structural determination.
  • Density Functional Theory (DFT) computations.

Main Results:

  • Successful synthesis and characterization of the first rhena-phenalene complexes.
  • Observation of Hückel aromaticity, σ-aromaticity, and pseudo π anti-aromaticity.
  • DFT calculations indicated the fused naphthyl ring induces anti-aromaticity and paramagnetic properties.

Conclusions:

  • Rhena-phenalene complexes display a unique combination of aromatic and anti-aromatic characteristics.
  • The fused naphthyl ring plays a key role in inducing pseudo π anti-aromaticity.
  • These findings expand the understanding of aromaticity in metallaaromatic systems.