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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

796
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
2.6K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.0K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
3.0K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.0K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.0K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
3.8K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.6K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Updated: May 24, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Chiroptical Signature and Absolute Configuration of Tröger's Base-Based Triangular Macrocycles.

Luis Palomo1, Carlos M Cruz2, Araceli G Campaña2

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Determining the 3D structure of chiral macrocycles like Tröger

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Spectroscopy

Background:

  • Chiral macrocycles are crucial for applications like asymmetric catalysis and chiral recognition.
  • Understanding their 3D structure is vital for unlocking their full potential.
  • Tröger's base-based macrocycles are of particular interest due to their unique topology.

Purpose of the Study:

  • To determine the absolute configuration (AC) of a Tröger's base-based triangular macrocycle, denoted as 3MC.
  • To establish a reliable method for AC determination of complex chiral macrocycles in solution.

Main Methods:

  • Vibrational and electronic chiroptical spectroscopy (ROA, CD).
  • Density Functional Theory (DFT) quantum chemistry calculations.
  • Analysis of molecular orbital topologies and electronic transition dipole moments.

Main Results:

  • DFT calculations accurately predicted the ROA spectra for both enantiomers of 3MC.
  • Experimental and theoretical Circular Intensity Difference (CID) spectra showed excellent agreement.
  • The study successfully correlated specific vibrational modes with electronic state transitions.

Conclusions:

  • The absolute configuration of the Tröger's base-based triangular macrocycle (3MC) was unambiguously determined in solution.
  • The combined use of chiroptical spectroscopy and DFT calculations provides a powerful approach for characterizing chiral macrocycles.
  • This methodology advances the understanding and application of complex chiral molecules in supramolecular chemistry.