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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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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...
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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes02:14

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

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The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were  initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified...
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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.3K
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.
3.3K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.3K
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...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

8.7K
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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Cannabichromene (CBC) Shows Matrix-Dependent Thermal Configurational Stability.

Simone Manetto1, Diego Caprioglio2, Gianpaolo Grassi3

  • 1Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, p.le A. Moro 5, 00185 Rome, Italy.

Journal of Natural Products
|December 9, 2024
PubMed
Summary
This summary is machine-generated.

The matrix affects the optical purity of cannabichromene (CBC) during decarboxylation. Solid surfaces significantly accelerate CBC racemization compared to solutions, impacting reported enantiomeric purity.

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Area of Science:

  • Cannabinoid chemistry and analysis
  • Chiral compound stability
  • Phytochemistry

Background:

  • Cannabichromene (CBC) is a significant phytocannabinoid with potential therapeutic applications.
  • The enantiomeric purity of CBC is crucial for its bioactivity and pharmacological effects.
  • Current understanding of CBC enantiopurity may be influenced by extraction and processing methods.

Purpose of the Study:

  • To investigate the impact of different matrices on the optical purity of cannabichromene (CBC) during thermolysis.
  • To evaluate the kinetics of thermal racemization of CBC in various solvents and on different surfaces.
  • To provide insights into discrepancies in reported CBC enantiomeric purity and suggest standardized protocols.

Main Methods:

  • Thermolysis of cannabichromenic acid (CBCA) in planta and in extracto at 130 °C.
  • Kinetic evaluation of thermal racemization of enantiopure CBC at 100 °C using enantioselective UHPLC.
  • Analysis of racemization in different solvents (decalin, isopropyl alcohol) and on surfaces (glass, cannabis biomass).

Main Results:

  • Thermolysis in planta caused a greater decrease in CBC enantiomeric excess (ee) than in extracto.
  • CBC racemization was significantly faster in isopropyl alcohol than in decalin, and dramatically accelerated on solid surfaces (t1/2 ~6 h).
  • Heating CBC on solid surfaces resulted in greater enantiopurity loss compared to heating in solution.

Conclusions:

  • The matrix, particularly solid surfaces, significantly influences the optical purity of CBC during decarboxylation.
  • Discrepancies in reported CBC enantiomeric purity may stem from decarboxylation protocols, not solely biogenesis.
  • Standardized decarboxylation protocols are essential for accurate assessment of CBC configurational status and its bioactivity.