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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.4K
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...
17.4K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.7K
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...
14.7K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.1K
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...
1.1K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.3K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
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...
3.5K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

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

1.4K
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.
1.4K

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A Mechanochromic Hydrogen-Bonded Rotaxane.

Rafael Sandoval-Torrientes1, ThomasR Carr1, Guillaume De Bo1

  • 1Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

Macromolecular Rapid Communications
|October 12, 2020
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Summary

Researchers developed a new fluorescent sensor that detects low pN forces, crucial for studying cellular and tissue mechanics in vivo. This versatile sensor offers tunable properties for various biological applications.

Keywords:
fluorescenceforce sensorsmechanochromismrotaxane

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Area of Science:

  • Biophysics
  • Materials Science
  • Chemical Biology

Background:

  • Tensile forces are critical for cellular and tissue functions.
  • Existing force sensors lack versatility and sensitivity for in vivo biological studies.
  • A need exists for adaptable sensors operating at low pN forces.

Purpose of the Study:

  • To develop a novel, versatile force sensor with tunable properties.
  • To create a sensor capable of detecting forces at the pN level.
  • To demonstrate the sensor's utility in a biological tissue model.

Main Methods:

  • Synthesis of a mechanoresponsive fluorescent hydrogen-bonded rotaxane incorporating a maleimide dye.
  • Characterization of the rotaxane's force-sensing capabilities.
  • Testing the sensor's performance in a polyacrylamide gel model.

Main Results:

  • A new rotaxane-based fluorescent force sensor was successfully synthesized.
  • The sensor demonstrated sensitivity to low pN forces.
  • The sensor's force-sensing properties were validated in a synthetic tissue model.

Conclusions:

  • The developed rotaxane is a promising tool for in vivo biomechanical studies.
  • This sensor offers a versatile platform for investigating biological processes driven by tensile forces.
  • The sensor's tunable nature allows for adaptation to diverse research needs.