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Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
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...
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.
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.
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...

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Related Experiment Video

Updated: May 13, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

2-Amino-N,3-dimethyl-benzamide.

Xiang-Dong Mei1, Yan-Hui Liang, Ke-Bin Li

  • 1State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study details the crystal structure of a C9H12N2O compound, revealing specific molecular arrangements and hydrogen bonding patterns. The findings highlight the compound's intermolecular interactions and structural characteristics in a crystalline state.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Supramolecular chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic compounds is crucial for predicting their properties.
  • Hydrogen bonding plays a significant role in the self-assembly and stability of molecular crystals.
  • Detailed structural analysis provides insights into chemical reactivity and material science applications.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound (C9H12N2O).
  • To investigate the presence and geometry of intramolecular and intermolecular hydrogen bonds.
  • To describe the supramolecular architecture formed by the compound in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided geometric information.
  • Intermolecular interaction analysis, including hydrogen bond detection, was performed.

Main Results:

  • The crystal structure of C9H12N2O was determined, showing a dihedral angle of 33.93(7)° between the amide group and the benzene ring.
  • An intramolecular N-H⋯O hydrogen bond was identified within the molecule.
  • Intermolecular N-H⋯N and N-H⋯O hydrogen bonds link molecules into double-stranded chains along the b axis.

Conclusions:

  • The title compound exhibits a specific non-planar conformation due to the dihedral angle between the amide and benzene moieties.
  • Intramolecular hydrogen bonding contributes to the molecule's conformational stability.
  • The observed intermolecular hydrogen bonding network dictates the formation of a unique double-stranded chain supramolecular structure in the crystal.