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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Butyl-anilinium perchlorate.

Xing-Wei Cai1, Hong-Fei Lu

  • 1School of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|August 13, 2011
PubMed
Summary

The crystal structure of 4-butyl-anilinium perchlorate reveals mirror-symmetric cations and anions. These molecules form a unique crystal structure through trifurcated hydrogen bonding between the cation and anion.

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Area of Science:

  • Crystallography
  • Solid-state chemistry

Background:

  • Anilinium salts are organic compounds with potential applications in materials science.
  • Understanding the crystal packing and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

  • To determine the crystal structure of 4-butyl-anilinium perchlorate.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the molecular and crystal structure.
  • Analysis of the crystal structure involved identifying symmetry elements and hydrogen bonding networks.

Main Results:

  • The crystal structure of 4-butyl-anilinium perchlorate was successfully determined.
  • Both the 4-butyl-anilinium cation and the perchlorate anion exhibit mirror symmetry.
  • Trifurcated N-H⋯O hydrogen bonding was identified as the primary interaction between the cation and anion.

Conclusions:

  • The observed symmetry and hydrogen bonding pattern provide insights into the self-assembly of this salt.
  • The findings contribute to the understanding of structure-property relationships in anilinium-based materials.