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Related Concept Videos

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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Structure of Amines01:19

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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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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Bispidine Platform as a Tool for Studying Amide Configuration Stability.

Dmitry P Krut'ko1, Alexey V Medved'ko2, Konstantin A Lyssenko1

  • 1Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, 119991 Moscow, Russia.

Molecules (Basel, Switzerland)
|January 21, 2022
PubMed
Summary

This study explored 3,7-diacyl bispidine conformations using NMR. Different acyl groups influenced syn/anti-isomer ratios, revealing new dynamic processes and amide bond inversion mechanisms.

Keywords:
3,7-diazabicyclo[3.3.1]nonanesNMR spectroscopyX-ray diffraction studybarriers of amide rotationdynamic stereochemistryquantum chemical calculations

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Area of Science:

  • Organic Chemistry
  • Structural Chemistry
  • Spectroscopy

Background:

  • Bispidines are nitrogen-containing bicyclic compounds with diverse applications.
  • Understanding their solution and solid-state conformations is crucial for predicting their properties and reactivity.
  • Previous studies have not extensively explored the conformational dynamics of 3,7-diacyl bispidines with various acyl substituents.

Purpose of the Study:

  • To investigate the solution conformations of seventeen 3,7-diacyl bispidines using NMR spectroscopy.
  • To determine the influence of different acyl groups (alkyl, alkenyl, aryl, hetaryl, ferrocene) on the syn/anti-isomer ratios.
  • To elucidate the mechanisms of amide bond inversion and other dynamic processes in these compounds.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy, including Variable Temperature (VT) NMR experiments.
  • X-ray crystallography for solid-state structure determination.
  • Quantum chemical calculations to model conformational transformations and reaction mechanisms.

Main Results:

  • NMR analysis revealed distinct syn/anti-isomer ratios depending on the acyl group substituents in solution.
  • A chiral bispidine derivative exhibited a novel dynamic process involving rotation around the CO-C=C bond, in addition to amide inversion.
  • X-ray crystallography provided insights into the solid-state structures, with the unique syn-form observed in an acyclic bispidine-based bis-amide crystal.
  • Quantum chemical calculations uncovered an unexpected amide bond inversion mechanism, proceeding via a chair-boat conformation.

Conclusions:

  • The nature of acyl groups significantly impacts the conformational preferences of 3,7-diacyl bispidines in solution.
  • New dynamic processes, including amide bond inversion and rotation around specific bonds, were identified and quantified.
  • The study provides a deeper understanding of the conformational behavior and reaction mechanisms of bispidine derivatives, with implications for their design and application.