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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.1K
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...
3.1K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
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.
2.1K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.5K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.5K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.4K
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,...
9.4K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

15.9K
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...
15.9K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

13.6K
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...
13.6K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation.

Yanjun Ding1, Lukman O Alimi1, Jing Du2

  • 1Smart Hybrid Materials (SHMs) Laboratory, Advanced Membranes and Porous Materials Center, King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Kingdom of Saudi Arabia niveen.khashab@kaust.edu.sa.

Chemical Science
|April 13, 2022
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Summary

Pillar[3]trianglamine (P-TA) macrocycles selectively separate 1-hexene (1-He) from its isomer trans-3-hexene (trans-3-He) using molecular sieving. This breakthrough enables efficient, multi-cycle separation in both vapor and liquid states for industrial applications.

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Area of Science:

  • Supramolecular Chemistry
  • Separation Science
  • Materials Chemistry

Background:

  • Separating alpha-olefins from isomers is difficult due to similar physical properties.
  • Existing methods face challenges with efficiency and energy consumption.

Purpose of the Study:

  • To synthesize pillar[3]trianglamine (P-TA) macrocycles for selective olefin isomer separation.
  • To investigate the mechanism of selective adsorption and the performance of P-TA in different states.

Main Methods:

  • Synthesis of allyl-functionalized P-TA macrocycles.
  • Vapor and liquid phase sorption experiments.
  • Single-crystal X-ray diffraction and powder X-ray diffraction.
  • Column chromatography using P-TA modified silica sieves.

Main Results:

  • P-TA macrocycles demonstrated selective separation of 1-hexene (1-He) from trans-3-hexene (trans-3-He).
  • Selective adsorption is attributed to stable host-guest complex formation.
  • Separation was effective in both vapor and liquid states, with reversible performance over multiple cycles.
  • P-TA modified silica sieves showed utility in chromatographic separation.

Conclusions:

  • P-TA macrocycles offer a promising solution for challenging olefin isomer separations.
  • The developed method supports sustainable and energy-efficient industrial separation practices.
  • Macrocyclic hosts can serve as effective molecular recognition units in practical separation technologies.