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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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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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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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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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Molecules and Compounds02:38

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Atoms and Molecules
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Activation Energy01:26

Activation Energy

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Activation energy is the minimum amount of energy necessary for a chemical reaction to move forward. The higher the activation energy, the slower the rate of the reaction. However, adding heat to the reaction will increase the rate, since it causes molecules to move faster and increase the likelihood that molecules will collide. The collision and breaking of bonds represents the uphill phase of a reaction and generates the transition state. The transition state is an unstable high-energy state...
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tRNA Activation02:26

tRNA Activation

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Aminoacyl-tRNA synthetases are present in both eukaryotes and bacteria. Though eukaryotes have 20 different aminoacyl-tRNA synthetases to couple to 20 amino acids, many bacteria do not have genes for all of these aminoacyl-tRNA synthetases. Despite this, they still use all 20 amino acids to synthesize their proteins. For instance, some bacteria do not have the gene encoding the enzyme that couples glutamine with its partner tRNA. In these organisms, one enzyme adds glutamic acid to all of the...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Small molecule activation by boron-containing heterocycles.

Yuanting Su1, Rei Kinjo

  • 1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Nanyang Link 21, Singapore 637371, Singapore. rkinjo@ntu.edu.sg.

Chemical Society Reviews
|April 13, 2019
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Summary

Boron-containing heterocycles are emerging as powerful tools for activating small molecules, challenging the traditional role of metal complexes in chemical transformations. This review explores their mechanisms for breaking sigma and pi bonds.

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Area of Science:

  • Main group chemistry
  • Organoboron chemistry
  • Catalysis

Background:

  • Metal complexes traditionally dominate small molecule fixation and transformation.
  • Recent advances in main group chemistry offer alternatives to transition metals.
  • Boron-based systems show promise in mimicking metal complex reactivity.

Purpose of the Study:

  • To review boron-containing heterocycles for small molecule activation.
  • To elucidate the mechanisms behind sigma- and pi-bond activation by these systems.
  • To highlight the growing importance of main group chemistry in catalysis.

Main Methods:

  • Literature review of boron-containing heterocycles.
  • Analysis of reaction mechanisms for small molecule activation.
  • Focus on systems activating sigma- and pi-bonds.

Main Results:

  • Boron-containing heterocycles effectively mediate small molecule activation.
  • Demonstrated ability to activate both sigma- and pi-bonds.
  • Mechanistic insights into these activation processes are provided.

Conclusions:

  • Boron heterocycles represent a significant advancement in main group chemistry.
  • They offer a viable alternative to metal complexes for small molecule activation.
  • Further research into these systems will expand catalytic possibilities.