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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Exceptionally effective benzene/cyclohexane separation using a nitro-decorated metal-organic framework.

Aleksandr A Sapianik1, Konstantin A Kovalenko, Denis G Samsonenko

  • 1Nikolaev Institute of Inorganic Chemistry SB RAS, 3 Akad. Lavrentiev Av., 630090 Novosibirsk, Russia. sapianik@niic.nsc.ru.

Chemical Communications (Cambridge, England)
|June 20, 2020
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Summary

Researchers used metal-organic frameworks (MOFs) to selectively separate benzene and cyclohexane. Weak interactions between benzene and the MOF framework drive this efficient adsorption process.

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Separation Science

Background:

  • Selective separation of benzene and cyclohexane is crucial in chemical processes.
  • Existing separation methods can be energy-intensive or inefficient.
  • Metal-Organic Frameworks (MOFs) offer tunable pore sizes for molecular sieving.

Purpose of the Study:

  • To investigate the selective separation of benzene and cyclohexane using isoreticular MOFs.
  • To understand the role of void connection diameters in separation efficiency.
  • To elucidate the adsorption mechanism driving the separation.

Main Methods:

  • Synthesis of a series of isoreticular MOFs with systematically varied void connection diameters.
  • Testing the selective adsorption of benzene and cyclohexane in both liquid and vapor phases.
  • Characterization of host-guest interactions using adsorption studies.

Main Results:

  • Demonstrated selective separation of benzene from cyclohexane in both liquid and vapor phases.
  • Correlated separation efficiency with the diameter of void connections in the MOFs.
  • Identified weak interactions between benzene molecules and the MOF framework as the primary driving force for adsorption.

Conclusions:

  • Isoreticular MOFs with tailored void connections are effective for benzene/cyclohexane separation.
  • The size of the MOF's void connections is a critical parameter for selective adsorption.
  • Understanding adsorption interactions enables the design of advanced MOF-based separation materials.