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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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 the...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Density functional computational studies on (E)-2-[(2-Hydroxy-5-nitrophenyl)-iminiomethyl]-4-nitrophenolate.

Hasan Tanak1, Metin Yavuz

  • 1Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, Samsun, Turkey. htanak@omu.edu.tr

Journal of Molecular Modeling
|July 4, 2009
PubMed
Summary

This study used density functional theory to analyze a nitrophenolate compound, revealing key insights into its electronic structure and solvent interactions. The isodensity polarized continuum model (IPCM) proved more effective for predicting stability in different solvents.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Molecular Modeling

Background:

  • The title compound, (E)-2-[(2-hydroxy-5-nitrophenyl)-iminiomethyl]-4-nitrophenolate, is a complex organic molecule with potential applications requiring understanding of its electronic properties.
  • Investigating molecular structure, charge distribution, and energetic behavior in various environments is crucial for predicting chemical reactivity and stability.

Purpose of the Study:

  • To perform a comprehensive theoretical investigation of the title compound using density functional calculations.
  • To elucidate the atomic charges, molecular electrostatic potential, and thermodynamic functions.
  • To examine the energetic behavior and structural stability in different solvent media.

Main Methods:

  • Density functional theory (DFT) calculations were employed using the B3LYP functional with the 6-31G(d,p) basis set.
  • Solvent effects were modeled using both the Onsager method and the isodensity polarized continuum model (IPCM).
  • Natural Bond Orbital (NBO) and Frontier Molecular Orbital (FMO) analyses were conducted to understand electronic properties.

Main Results:

  • Calculations revealed significant negative charges on phenolate and nitro group oxygen atoms, influencing their coordination abilities.
  • The IPCM method predicted a more stable structure for the compound in solvent media compared to the Onsager method.
  • NBO and FMO analyses provided detailed insights into the electronic structure and orbital interactions.

Conclusions:

  • The electronic structure and charge distribution of the title compound are significantly influenced by the presence of nitro and hydroxyl groups.
  • The choice of solvation model impacts the predicted stability, with IPCM offering a more accurate representation.
  • This theoretical study provides valuable data for understanding the chemical behavior and potential applications of this nitrophenolate derivative.