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Related Concept Videos

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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.

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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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3-Methyl-anilinium hydrogen phthalate.

Ming-Liang Liu1

  • 1College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 20, 2012
PubMed
Summary

This study details the crystal structure of a salt formed by 3-methyl-phenyl-ammonium cations and hydrogen phthalate anions. The structure reveals strong hydrogen bonding interactions within the anions and between cations and anions, forming layered crystal structures.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding the crystal packing and intermolecular interactions of organic salts is crucial for designing new materials.
  • Hydrogen phthalate anions are known to form intricate hydrogen-bonded networks.

Purpose of the Study:

  • To elucidate the crystal structure of the salt formed between 3-methyl-phenyl-ammonium and hydrogen phthalate.
  • To investigate the hydrogen bonding patterns and their influence on the crystal architecture.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of intra- and intermolecular hydrogen bonds (O-H⋯O, N-H⋯O) was performed.

Main Results:

  • The asymmetric unit contains two 3-methyl-phenyl-ammonium cations and two hydrogen phthalate anions.
  • Planar hydrogen phthalate anions exhibit strong intramolecular O-H⋯O hydrogen bonds.
  • A corrugated layered structure is formed through extensive N-H⋯O hydrogen bonds between cations and anions, oriented parallel to the (001) plane.

Conclusions:

  • The crystal structure is stabilized by a combination of intramolecular hydrogen bonds within the anion and intermolecular hydrogen bonds forming a layered architecture.
  • The observed hydrogen bonding network dictates the overall supramolecular arrangement in the solid state.