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Related Concept Videos

Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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Thermal Electrocyclic Reactions: Stereochemistry

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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.
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SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

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The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
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Cooperative Allosteric Transitions

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Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks
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A bi-stable Pt(II) based molecular turnstile.

Nicolas Zigon1, Mir Wais Hosseini

  • 1Molecular Tectonics Laboratory, UMR UDS-CNRS, 7140 & icFRC, Université de Strasbourg, F-67000, Strasbourg, France. hosseini@unistra.fr.

Chemical Communications (Cambridge, England)
|July 7, 2015
PubMed
Summary

Researchers designed a novel organometallic turnstile that switches between two states using hydrogen bonds and metal ion coordination. This reversible switching mechanism offers potential for advanced molecular devices.

Area of Science:

  • Supramolecular Chemistry
  • Organometallic Chemistry
  • Molecular Machines

Background:

  • The design of molecular machines with controllable dynamics is crucial for developing advanced functional materials.
  • Organometallic complexes offer versatile platforms for constructing sophisticated molecular architectures.
  • The interplay between non-covalent interactions like hydrogen bonds and coordination bonds can be exploited to control molecular motion.

Purpose of the Study:

  • To design and synthesize a bi-stable, unsymmetrical organometallic turnstile.
  • To investigate the dynamic behavior of the designed turnstile in solution.
  • To explore the switching mechanism between different conformational states driven by hydrogen bonding and metal ion coordination.

Main Methods:

  • Design and synthesis of a novel organometallic complex featuring a platinum(II) center.

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  • Utilized Nuclear Magnetic Resonance (NMR) spectroscopy to study the dynamic behavior in solution.
  • Investigated the effect of silver(I) cations as a metallic effector to induce conformational changes.

    • Main Results:

    • A bi-stable organometallic turnstile was successfully designed, exhibiting two distinct conformational states.
    • In the absence of metal ions, the turnstile is locked via a hydrogen bond between phenol and pyridyl groups.
    • Addition of silver(I) cations induces a reversible switch to a new closed state through coordination bonding with pyridyl units.

    Conclusions:

    • The study demonstrates the successful construction of a switchable organometallic turnstile controlled by competing hydrogen and coordination bonds.
    • The reversible switching behavior highlights the potential of this system for applications in molecular switches and responsive materials.
    • This work provides insights into the rational design of dynamic molecular systems based on metal-ligand interactions.