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Related Concept Videos

Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred to as...
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Divergence and Curl of Magnetic Field

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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...
¹H NMR: Interpreting Distorted and Overlapping Signals01:02

¹H NMR: Interpreting Distorted and Overlapping Signals

Spin systems where the difference in chemical shifts of the coupled nuclei is greater than ten times J are called first-order spin systems. These nuclei are weakly coupled, and their chemical shifts and coupling constant can generally be estimated from the well-separated signals in the spectrum.
As Δν decreases and the signals move closer, the doublets appear increasingly distorted. The intensities of the inner lines increase at the cost of those of the outer lines as the signals are slanted or...
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...

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Stepwise helicity inversions by multisequential metal exchange.

Shigehisa Akine1, Shiho Sairenji, Takanori Taniguchi

  • 1Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan. akine@chem.tsukuba.ac.jp

Journal of the American Chemical Society
|August 14, 2013
PubMed
Summary

Researchers developed a novel molecular system for stepwise, multi-sequential helicity inversion. This breakthrough in functional molecular chemistry enables dynamic regulation with multiple asymmetric functions.

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Area of Science:

  • Functional Molecular Chemistry
  • Supramolecular Chemistry
  • Coordination Chemistry

Background:

  • Developing artificial helical molecules with responsive helicity inversion is a significant challenge.
  • Existing methods primarily focus on single-mode transitions between right- and left-handed states.

Purpose of the Study:

  • To report the first molecular system enabling stepwise, multi-sequential helicity inversion.
  • To demonstrate a novel approach using metal exchange in helical complexes.

Main Methods:

  • Utilized a hexaoxime ligand (H6L(1)) to form helical complexes.
  • Performed sequential metal addition (Zn(2+), Ba(2+), La(3+)) to induce stepwise molecular conversion.
  • Monitored associated changes in molecular helicity.

Main Results:

  • The ligand H6L(1) underwent a four-step conversion upon sequential metal addition.
  • Achieved a three-step helicity inversion: right-handed → left-handed → right-handed → left-handed.
  • Demonstrated the first example of stepwise, multi-mode helicity inversion in a discrete molecule.

Conclusions:

  • The developed molecular system offers a new platform for dynamic regulation.
  • Potential applications in constructing systems with multiple, switchable asymmetric functions.
  • Opens new avenues for advanced functional molecular materials.