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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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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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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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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Systematic Approach to Negative Fukui Functions: Its Association with Nitro Groups in Aromatic Systems.

Pedro Pablo Zamora Yates1, Klaus Bieger1

  • 1Departamento de Química y Biología, Facultad de Ciencias Naturales, Universidad de Atacama, Av. Copayapu 485, Copiapó 1530000, Chile.

International Journal of Molecular Sciences
|January 11, 2025
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Summary

Negative Fukui functions, unexplained by electron density, are linked to nitro groups on aromatic systems. This study clarifies their chemical reactivity and the impact of nitro group orientation.

Keywords:
Density Functional Theory (DFT)chemical reactivitynegative Fukui functionnitro groups

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Area of Science:

  • Quantum Chemistry
  • Theoretical Chemistry
  • Chemical Reactivity

Background:

  • Fukui functions relate to electron densities, aiding reactivity predictions.
  • Negative Fukui functions lack clear interpretation within electron density models.
  • Existing literature suggests negative values correlate with wave function nodes.

Purpose of the Study:

  • Investigate the phenomenon of negative Fukui functions.
  • Relate negative Fukui functions to specific chemical moieties and their electronic properties.
  • Understand and predict chemical reactivity associated with negative Fukui functions.

Main Methods:

  • Computational analysis of Fukui functions.
  • Correlation of negative Fukui function values with the presence and position of nitro groups.
  • Examination of the influence of nitro group orientation relative to aromatic systems.

Main Results:

  • Negative Fukui function values are demonstrably linked to the presence of nitro groups.
  • Nitro groups, as electron-withdrawing moieties, exhibit high highest occupied molecular orbital (HOMO) electron densities near zero.
  • The orientation of the nitro group significantly influences the observed Fukui function values.

Conclusions:

  • Negative Fukui functions can be understood in the context of nitro-substituted aromatic systems.
  • This research provides a framework for predicting chemical reactivity based on negative Fukui function values.
  • The findings offer insights into the electronic behavior of electron-withdrawing groups in aromatic systems.