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Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

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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.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
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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.
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Diazonium Group Substitution: –OH and –H01:19

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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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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Dimethyl-ammonium 4-nitro-phenolate-4-nitro-phenol (1/1).

Jing-Mei Xiao1

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study synthesized a novel compound from dimethylamine and 4-nitrophenol, achieving an 85% yield. The crystal structure reveals significant hydrogen bonding, forming chains along the b-axis.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the synthesis and structural properties of novel organic compounds is crucial in materials science.
  • Investigating intermolecular interactions, such as hydrogen bonding, provides insights into crystal packing and material stability.

Purpose of the Study:

  • To synthesize and characterize a new compound formed from dimethylamine and 4-nitrophenol.
  • To elucidate the crystal structure and hydrogen bonding network of the synthesized compound.

Main Methods:

  • Chemical synthesis involving dimethylamine and 4-nitrophenol.
  • Single-crystal X-ray diffraction to determine molecular and crystal structure.
  • Analysis of dihedral angles and hydrogen bond distances.

Main Results:

  • Successful synthesis of the title compound with an 85% yield.
  • Determination of dihedral angles between phenyl rings and nitro groups (5.7° and 2.5°).
  • Identification of strong hydrogen bonds forming a chain along the b-axis.

Conclusions:

  • The synthesized compound exhibits a well-defined crystal structure with significant intermolecular hydrogen bonding.
  • The observed hydrogen bonding network influences the crystal packing and supramolecular architecture.
  • This study contributes to the understanding of organic salt formation and crystal engineering.