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Electrophilic Addition to Alkynes: Halogenation02:38

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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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A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
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Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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Spectroscopic Implications for [N-X-N]+ (X = I, Br)-Type Halonium Compounds with Formal Hypervalency.

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  • 1Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima-shi, Hiroshima 739-8526, Japan.

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Bis(pyridine)halonium complexes exhibit unique electronic structures. Spectroscopic analysis reveals charge-transfer transitions and quantifies halogen bond strength, offering new insights into hypervalency.

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Area of Science:

  • Inorganic Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Bis(pyridine)halonium complexes ([Py2X]+) are hypervalent species with 10 valence electrons.
  • Understanding the electronic structure and bonding in these complexes is crucial for advancing hypervalency research.

Purpose of the Study:

  • To investigate the gas-phase UV spectra of bis(pyridine)halonium complexes ([Py2X]+).
  • To elucidate the electronic states and bonding characteristics of these hypervalent species.
  • To provide a spectroscopic perspective on hypervalency.

Main Methods:

  • Gas-phase UV spectroscopy using a cryogenic ion trap.
  • Analysis of vibronic structures and spectral band characteristics.
  • Quantitative estimation of N-X bond force constants.

Main Results:

  • Observed distinct vibronic structures for charge-transfer (CT) transitions, indicating halogen bonds.
  • Identified broad spectral bands at higher energies attributed to three-center, four-electron (3c-4e) bond orbitals.
  • Proposed charge-resonance (CR) interactions between charge-localized states to describe electronic states.
  • Quantitatively estimated N-X bond force constants for X=Br (159 N·m⁻¹) and X=I (132 N·m⁻¹).

Conclusions:

  • The electronic states of [Py2X]+ complexes are influenced by significant charge-resonance interactions.
  • Spectroscopic data provides a new perspective on the nature of hypervalency.
  • The observed differences in force constants correlate with the magnitude of electron transfer during CT excitation.