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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
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.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Electrophilic Addition to Alkynes: Halogenation02:38

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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2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)01:19

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

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Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

3.9K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.4K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.4K
¹H NMR: Pople Notation01:09

¹H NMR: Pople Notation

2.4K
The Pople nomenclature system classifies spin systems based on the difference between their chemical shifts. Coupled spins are denoted by capital letters with subscripts indicating the number of equivalent nuclei. When the coupled nuclei have well-separated chemical shifts, they are assigned letters that are far apart in the alphabet, such as A and X. When the difference in chemical shifts is small, coupled nuclei are named using adjacent letters of the alphabet (AB, MN, or XY).
A proton...
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Synthesis and One-Electron Reduction of Donor-Acceptor-Stabilized Si<sup>II</sup>-E<sup>II</sup>-Si<sup>II</sup> Trimetallylenes (E = Ge, Sn, Pb).

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Generation of Zerovalent Metal Core Nanoparticles Using n-2-aminoethyl-3-aminosilanetriol
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An isolable NHC-supported silanone.

Yun Xiong1, Shenglai Yao, Matthias Driess

  • 1Institute of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 135, Sekr. C2, D-10623 Berlin, Germany.

Journal of the American Chemical Society
|May 14, 2009
PubMed
Summary

Researchers synthesized a unique silanone complex via facile oxygenation of a nucleophilic silicon(II) precursor. This discovery advances understanding of silicon-oxygen bonding and stable silanone synthesis.

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Area of Science:

  • Inorganic Chemistry
  • Organosilicon Chemistry
  • Coordination Chemistry

Background:

  • Stable silicon compounds are crucial in materials science and catalysis.
  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Silylenes, silicon analogs of carbenes, exhibit unique reactivity.

Purpose of the Study:

  • To synthesize and characterize a novel isolable silanone complex.
  • To investigate the reactivity of a highly nucleophilic NHC-silylene precursor.
  • To elucidate the electronic structure of the Si=O bond in the resulting silanone.

Main Methods:

  • Synthesis of a stable silylene precursor.
  • Reaction of the silylene with an N-heterocyclic carbene at low temperature (-60°C).
  • Facile oxygenation of the NHC-silylene complex to form the silanone.
  • Characterization of the silanone complex, including X-ray diffraction.

Main Results:

  • Successfully synthesized and isolated a unique isolable silanone complex (3) in 94% yield.
  • The NHC-silylene precursor (2) exhibited unusually high nucleophilicity.
  • The silanone complex displayed a remarkably short Si=O bond distance (1.541(2) Å).

Conclusions:

  • The short Si=O bond suggests a betaine-like pi system with balanced electrostatics.
  • This work demonstrates a facile route to stable silanones.
  • The findings contribute to the understanding of silicon-oxygen bonding and reactivity.