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Crown Ethers02:36

Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...
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Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Structural Isomerism02:34

Structural Isomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
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Ionic Bonding and Electron Transfer02:48

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Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions. 
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Valence Bond Theory

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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Structures of Alkali Metal Ion-Crown Ether 1:2 Heterocomplexes Investigated Using Cold Gas-Phase Spectroscopy.

Yoshiya Inokuchi1, Thomas R Rizzo2

  • 1Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, Hiroshima 739-8526, Japan.

The Journal of Physical Chemistry. A
|September 16, 2025
PubMed
Summary

Alkali metal ion-crown ether heterocomplexes were studied in the gas phase. Rb+ and Cs+ ions were mainly encapsulated by 18-crown-6 (18C6), differing from K+ complexes where ion transfer occurred.

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Crown ethers (CEs) are macrocyclic polyethers known for their ability to selectively bind alkali metal cations.
  • Heterocomplexes involving multiple crown ethers and alkali metal ions offer unique structural and binding properties.
  • Understanding these complexes is crucial for applications in ion separation, sensing, and catalysis.

Purpose of the Study:

  • To determine the gas-phase structures and intermolecular interactions of alkali metal ion-crown ether 1:2 heterocomplexes.
  • To investigate the influence of different crown ethers (benzo-18-crown-6, dibenzo-18-crown-6, and 18-crown-6) on complex stability and structure.
  • To compare the behavior of rubidium (Rb+) and cesium (Cs+) complexes with previously studied potassium (K+) complexes.

Main Methods:

  • Experimental study of alkali metal ion-crown ether heterocomplexes (M+ (DB18C6)(18C6) and M+ (B18C6)(18C6), M = Rb, Cs) under cold (∼10 K) gas-phase conditions.
  • Characterization using ultraviolet (UV) and infrared (IR) spectroscopy.
  • Support and interpretation of spectral data through quantum chemical calculations.

Main Results:

  • Electronic transitions for M+(DB18C6)(18C6) and M+(B18C6)(18C6) complexes were observed near those of the respective DB18C6 and B18C6 monomers.
  • The M+ ion was primarily encapsulated by the 18-crown-6 (18C6) moiety, with weaker binding of DB18C6 and B18C6.
  • UV photodissociation (UVPD) yielded M+(18C6) as the main fragments, consistent with 18C6 encapsulation, but highlighted a unique K+ ion transfer in K+(B18C6)(18C6).

Conclusions:

  • The interaction between the alkali metal ion and the larger crown ethers (DB18C6, B18C6) is significantly weaker in the 1:2 heterocomplexes compared to 1:1 complexes.
  • Gas-phase structures reveal preferential encapsulation of Rb+ and Cs+ by 18C6, trapping high-energy conformers due to incomplete relaxation.
  • The UVPD patterns underscore the distinct behavior of K+(B18C6)(18C6), where UV excitation induces K+ transfer from 18C6 to B18C6.