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Related Concept Videos

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

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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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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Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

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It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
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¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

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

1.8K
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.
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

12.0K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

21.6K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
21.6K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

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Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
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Spin Saturation Transfer Difference NMR SSTD NMR: A New Tool to Obtain Kinetic Parameters of Chemical Exchange Processes
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Conformational Effects on Specific Rotation: A Theoretical Study Based on the S̃k Method.

Marco Caricato1

  • 1Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.

The Journal of Physical Chemistry. A
|July 14, 2015
PubMed
Summary
This summary is machine-generated.

This study analyzes specific rotation in chiral molecules like 2-carene and 3-methylcyclopentanone. A few key configurations explain differences in rotation, aiding prediction of molecular properties.

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Area of Science:

  • Computational Chemistry
  • Molecular Spectroscopy
  • Chiroptical Properties

Background:

  • Specific rotation is a fundamental property of chiral molecules.
  • Understanding the factors influencing specific rotation is crucial for chemical analysis and drug development.
  • Conformational flexibility can significantly impact a molecule's chiroptical properties.

Purpose of the Study:

  • To investigate the difference in specific rotation between stable conformers of (S)-(+)-2-carene and (R)-3-methylcyclopentanone.
  • To analyze specific rotation using rotational strength in configuration space (S̃k).
  • To identify the key molecular orbital contributions to specific rotation.

Main Methods:

  • Calculation of specific rotation for stable conformers of two test chiral molecules.
  • Analysis of rotational strength in configuration space (S̃k).
  • Examination of occupied-virtual molecular orbital pair contributions.

Main Results:

  • Specific rotation differences between conformers were analyzed.
  • Rotational strength analysis revealed contributions from numerous excited configurations.
  • A limited set of configurations was found sufficient to explain sign and magnitude variations in specific rotation among conformers.

Conclusions:

  • The study provides insights into the electronic origins of specific rotation differences in chiral molecules.
  • The findings suggest that specific rotation can be understood and potentially predicted by analyzing key configurations.
  • This work offers a promising approach for the theoretical prediction of chiroptical properties.