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Degree of Unsaturation02:05

Degree of Unsaturation

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The degree of unsaturation (U), or index of hydrogen deficiency (IHD), is defined as the difference in the number of pairs of hydrogen atoms between the compound and the acyclic alkane with the same number of carbon atoms. Each double bond or ring costs two hydrogen atoms compared to a saturated analog and results in one degree of unsaturation.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
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Basicity of Aromatic Amines01:18

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
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Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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σ-Aromaticity in a Fully Unsaturated Ring.

Jingjing Wu1, Xin Liu1, Yulei Hao1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.

Chemistry, an Asian Journal
|September 21, 2018
PubMed
Summary
This summary is machine-generated.

This study reveals that σ-aromaticity can exist in unsaturated systems, challenging traditional views. We found a strong correlation between nucleus-independent chemical shift (NICS) and extra cyclic resonance energies (ECREs) in cyclopropene derivatives.

Keywords:
cyclopropenemetalla-aromaticitymethylenecyclopropeneunsaturated ringsσ-aromaticity

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Area of Science:

  • Organic Chemistry
  • Theoretical Chemistry
  • Quantum Chemistry

Background:

  • Aromaticity is a key concept in chemistry, with σ- and π-aromaticity describing electron delocalization in saturated and unsaturated rings, respectively.
  • Traditional understanding reserves π-aromaticity for unsaturated systems and σ-aromaticity for saturated ones.

Purpose of the Study:

  • To investigate the presence and evaluation of σ-aromaticity in unsaturated three-membered rings (3MRs).
  • To establish a correlation between nucleus-independent chemical shift (NICS) and extra cyclic resonance energies (ECREs) for assessing σ-aromaticity.

Main Methods:

  • Computational chemistry methods, including molecular orbital (MO) and valence bond (VB) theories, were employed.
  • Nucleus-independent chemical shift (NICS) values and extra cyclic resonance energies (ECREs) were computed.

Main Results:

  • A strong correlation was demonstrated between NICS values and ECREs in the unsaturated 3MR of cyclopropene.
  • The study identified σ-aromaticity in the fully unsaturated ring of methylenecyclopropene and its metallic analogs.

Conclusions:

  • The findings challenge the conventional understanding of σ-aromaticity, extending its applicability to unsaturated systems.
  • This research opens new possibilities for designing σ-aromaticity in systems previously considered exclusive to π-aromaticity.