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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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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
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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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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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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Molecular imine cages with π-basic Au3(pyrazolate) faces.

Noga Eren1, Farzaneh Fadaei-Tirani1, Rosario Scopelliti1

  • 1Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL) 1015 Lausanne Switzerland kay.severin@epfl.ch.

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|March 8, 2024
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Summary
This summary is machine-generated.

Researchers created novel gold cages using dynamic covalent chemistry. These cages effectively capture polyhalogenated aromatic compounds and fullerenes, showcasing advanced host-guest chemistry.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Development of novel host molecules for selective guest encapsulation remains a key challenge in supramolecular chemistry.
  • Gold complexes offer unique electronic properties for constructing advanced functional materials.

Purpose of the Study:

  • To synthesize and characterize novel supramolecular cages based on gold complexes.
  • To investigate the host-guest properties of these cages, particularly for π-acidic guests and fullerenes.

Main Methods:

  • Utilized dynamic covalent imine chemistry to connect pre-formed gold complexes.
  • Employed X-ray crystallography for structural elucidation of the cages and their guest adducts.

Main Results:

  • Successfully synthesized one tetrahedral and two trigonal prismatic cages featuring π-basic Au3(pyrazolate)3 faces.
  • Demonstrated enhanced π-acid interaction due to the parallel arrangement of gold complexes in prismatic cages, enabling encapsulation of polyhalogenated aromatic compounds.
  • Identified the tetrahedral cage as a potent receptor for C60 and C70 fullerenes.

Conclusions:

  • The study presents a novel strategy for constructing complex supramolecular architectures using gold coordination chemistry.
  • The designed cages exhibit significant potential for selective recognition and binding of challenging guests like polyhalogenated aromatics and fullerenes.
  • These findings open avenues for applications in molecular recognition, sensing, and materials science.