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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.8K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
16.8K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.4K
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...
1.4K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

11.7K
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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Conformations of Butane02:20

Conformations of Butane

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Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
19.8K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
16.7K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

4.7K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.7K

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Related Experiment Video

Updated: Mar 14, 2026

Solubility of Hydrophobic Compounds in Aqueous Solution Using Combinations of Self-assembling Peptide and Amino Acid
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Solubility of Hydrophobic Compounds in Aqueous Solution Using Combinations of Self-assembling Peptide and Amino Acid

Published on: September 20, 2017

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Solution Conformations of Curcumin in DMSO.

Cathryn A Slabber1, Craig D Grimmer1, Ross S Robinson1

  • 1School of Chemistry and Physics, University of KwaZulu-Natal , Pietermaritzburg, South Africa 3209.

Journal of Natural Products
|October 8, 2016
PubMed
Summary

NMR Analysis of Molecular Flexibility In Solution (NAMFIS) revealed four enol conformations for curcumin in DMSO. Two match crystal structures complexed with transthyretin, aiding molecular understanding.

Area of Science:

  • Biochemistry
  • Structural Biology
  • Chemical Physics

Background:

  • Curcumin exhibits diverse biological activities but its solution structure and flexibility remain incompletely understood.
  • Understanding curcumin's conformational landscape is crucial for elucidating its mechanism of action and for drug design.

Purpose of the Study:

  • To investigate the molecular flexibility and solution conformations of curcumin using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • To compare the solution structures of curcumin with its known solid-state structures.

Main Methods:

  • Application of the NMR Analysis of Molecular Flexibility In Solution (NAMFIS) technique.
  • Utilizing quantitative 1H-1H distance constraints derived from NMR data.
  • Computational analysis to identify and refine candidate molecular conformations.

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Main Results:

  • Identification of a solution collection comprising four distinct enol conformations of curcumin in DMSO.
  • Two of the identified solution conformations closely resemble the structure of curcumin crystallized with human transthyretin.
  • One conformation is highly similar to a previously determined single-crystal structure of curcumin.

Conclusions:

  • NAMFIS effectively elucidates curcumin's conformational dynamics in solution.
  • Solution conformations of curcumin show significant overlap with its solid-state structures, particularly when bound to transthyretin.
  • This study provides valuable insights into curcumin's structural behavior, relevant for its biological functions and therapeutic applications.