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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.0K
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).
7.0K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.8K
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,...
5.8K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.0K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
4.0K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.2K
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.
3.2K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.0K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
4.0K
Structure of Amines01:19

Structure of Amines

3.3K
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...
3.3K

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Pyrrole N-H Anion Complexes.

Gabriela I Vargas-Zúñiga1, Jonathan L Sessler1

  • 1Department of Chemistry, The University of Texas at Austin, 105 E. 24 Street, Stop A5300, Austin, Texas 78712-1224, USA.

Coordination Chemistry Reviews
|November 7, 2017
PubMed
Summary
This summary is machine-generated.

This review summarizes the development of synthetic pyrrole-based anion receptors, focusing on both macrocyclic and open-chain systems. It highlights natural pyrrolic compounds and their synthetic analogs for anion recognition.

Keywords:
Anion BindingHydrogen-bondingProdigiosinPyrroleReceptorRecognition

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Chemical Biology

Background:

  • Pyrrole-based anion receptors have a history dating back to the 1990s.
  • Development has focused on macrocyclic systems like expanded porphyrins and calixpyrroles.
  • Open-chain pyrrolic systems offer direct analogies to natural anion binding motifs but lack comprehensive review.

Purpose of the Study:

  • To provide a comprehensive review of de novo pyrrole-based anion receptor synthesis.
  • To summarize the anion recognition chemistry of naturally occurring pyrrolic systems.
  • To discuss synthetic analogues of natural pyrrolic anion binders.

Main Methods:

  • Literature review of synthetic pyrrole-based receptors.
  • Analysis of anion recognition properties of natural and synthetic pyrrolic compounds.
  • Discussion of structure-activity relationships in pyrrole-based anion binding.

Main Results:

  • Extensive development of macrocyclic pyrrole-based anion receptors has been achieved.
  • Open-chain pyrrolic systems show promise for anion recognition, mirroring natural motifs.
  • Prodigiosins and their synthetic analogues represent a key class of naturally occurring pyrrolic anion binders.

Conclusions:

  • A comprehensive understanding of pyrrole-based anion receptors, both synthetic and natural, is crucial.
  • Further research into open-chain systems and synthetic analogues can advance anion recognition technologies.
  • This review consolidates existing knowledge and identifies future research directions.