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Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

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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.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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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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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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

Diazonium Group Substitution: –OH and –H

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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 N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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N'-(2,6-Di-methyl-phen-yl)-N-phenyl-methanimidamide.

Ilyes Oubaha1, Arindam Saha1, Garry S Hanan1

  • 1Département de chimie, Université de Montréal, Complexe des sciences, 1375, Avenue Thérèse-Lavoie-Roux, Montréal, Québec, H2V 0B3, Canada.

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|November 12, 2025
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Summary
This summary is machine-generated.

This study details a novel N,N'-disubstituted acetamidine molecule. Its crystal structure reveals specific bond lengths and hydrogen bonding, forming infinite chains in the solid state.

Keywords:
acetamidinecrystal structurehydrogen bonding

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Acetamidines are versatile organic compounds with diverse applications.
  • Understanding the structure-property relationships of substituted acetamidines is crucial for designing new materials.

Purpose of the Study:

  • To synthesize and characterize a novel non-symmetrically N,N"-disubstituted acetamidine.
  • To elucidate the crystal structure and intermolecular interactions of the title compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonding, C-H···π interactions) was performed.

Main Results:

  • The title compound, C16H18N2, crystallizes in an E-syn configuration.
  • Distinct amine (1.366(1) Å) and imine (1.288(1) Å) bond lengths were observed in the amidine linkage.
  • Infinite C(4) chains were formed via strong N-H···N hydrogen bonds, with weak C-H···π interactions also present.

Conclusions:

  • The study provides detailed structural insights into a novel N,N"-disubstituted acetamidine.
  • The observed hydrogen bonding network dictates the formation of extended supramolecular structures.
  • The findings contribute to the understanding of crystal engineering principles for organic molecules.