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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.0K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Structure of Amines01:19

Structure of Amines

2.5K
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’...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.8K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
2.6K
Amines: Introduction01:07

Amines: Introduction

4.4K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Urea-Functionalized Heterocycles: Structure, Hydrogen Bonding and Applications.

Soma J Keszei1,2, Márk Váradi1, Rita Skoda-Földes1

  • 1Research Group of Organic Synthesis and Catalysis, University of Pannonia, Egyetem u. 10, 8200 Veszprém, Hungary.

Molecules (Basel, Switzerland)
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Ureido-heterocycles are versatile building blocks for advanced materials like supramolecular polymers and sensors. Their unique hydrogen-bonding capabilities enable diverse applications, particularly in biomedical fields.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Ureido-heterocycles exhibit diverse hydrogen-bonding patterns, enabling their use in supramolecular chemistry.
  • These compounds serve as crucial building blocks for advanced materials, including polymers, catalysts, and sensors.
  • The heterocyclic moiety offers additional hydrogen bonding sites and metal-binding capabilities, alongside responsiveness to external stimuli.

Purpose of the Study:

  • To review the structural features of ureido-heterocycles.
  • To discuss their self-assembly and complex formation influenced by tautomerization and conformational isomerism.
  • To highlight their applications in molecular architectures, supramolecular polymers, and biomedical fields, as well as in catalysis and sensing.

Main Methods:

  • Literature review of ureido-heterocycles.
  • Analysis of structural features, including tautomerization and conformational isomerism.
  • Compilation of examples demonstrating applications in supramolecular polymers, biomedical uses, catalysis, and sensing.

Main Results:

  • Ureido-heterocycles possess tunable triple- and quadruple hydrogen-bonding patterns.
  • Tautomerization and conformational isomerism significantly impact self-assembly and complex formation.
  • These derivatives are effective in constructing supramolecular polymers and have shown promise in biomedical applications, catalysis, and sensor development.

Conclusions:

  • Ureido-heterocycles are highly versatile building blocks for supramolecular materials.
  • Their structural diversity and responsive nature facilitate a wide range of applications.
  • Further exploration of these compounds is warranted for advancements in materials science and related fields.