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Related Concept Videos

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.
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.
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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L-Phenylalanine-4-nitrophenol (1/1).

V H Rodrigues1, M M R R Costa, E de Matos Gomes

  • 1CEMDRX, Departamento de Física, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, P-3004-516 Coimbra, Portugal. vhugo@pollux.fis.uc.pt

Acta Crystallographica. Section C, Crystal Structure Communications
|December 7, 2006
PubMed
Summary

This study details the crystal structure of a 1:1 adduct between L-phenylalanine and 4-nitrophenol. The structure is stabilized by hydrogen bonding and van der Waals interactions, revealing alternating polar and non-polar zones.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • L-phenylalanine is a naturally occurring amino acid.
  • 4-nitrophenol is an organic compound with industrial applications.
  • Adduct formation between organic molecules can lead to novel structural properties.

Purpose of the Study:

  • To elucidate the crystal structure of the 1:1 adduct formed between L-phenylalanine and 4-nitrophenol.
  • To investigate the intermolecular interactions stabilizing the adduct.
  • To understand the arrangement of polar and non-polar regions within the crystal.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding networks and van der Waals interactions was performed.
  • The zwitterionic nature of L-phenylalanine within the adduct was confirmed.

Main Results:

  • The 1:1 adduct crystallizes with L-phenylalanine in its zwitterionic form.
  • Strong hydrogen bonds connect the polar components of the molecules.
  • Van der Waals forces contribute to the stability of alternating non-polar and polar zones.

Conclusions:

  • The crystal structure of the L-phenylalanine-4-nitrophenol adduct is characterized by a specific arrangement of intermolecular forces.
  • The interplay of hydrogen bonding and van der Waals interactions dictates the overall structural organization.
  • This study provides insights into the solid-state behavior of amino acid-phenol co-crystals.