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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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.
π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0, resulting in...
Inductive Effects on Chemical Shift: Overview01:27

Inductive Effects on Chemical Shift: Overview

The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
Local Anesthetics: Mechanism of Action01:23

Local Anesthetics: Mechanism of Action

Local anesthetics (LAs) block sensory and motor impulses by inhibiting the sodium channels on the nerve cell membranes. This induces temporary loss of sensation, relieving pain in a specific body area.
Local anesthetics are amphiphilic molecules consisting of a hydrophobic aromatic part linked to a hydrophilic group by an ester or amide linkage. They are weak bases and are usually available as salts, which increases their solubility and stability. Once administered, LAs exist in the body either...
IR Absorption Frequency: Delocalization01:04

IR Absorption Frequency: Delocalization

Electron delocalization refers to the distribution of electrons across multiple atoms within a molecule rather than being confined to a single atom or bond. This phenomenon is common in systems with conjugated bonds—structures where alternating single and double bonds allow π-electrons to move freely across the network. The movement of electrons stabilizes the molecule and can affect various chemical properties, including vibrational frequencies observed in IR spectroscopy.
In IR spectroscopy,...

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A Technique to Functionalize and Self-assemble Macroscopic Nanoparticle-ligand Monolayer Films onto Template-free Substrates
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Localization vs conduction: anionic excitations in alkanethiol self-assembled monolayers.

Etienne Garand1, M Golam Moula, Paul A Rowntree

  • 1Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.

Langmuir : the ACS Journal of Surfaces and Colloids
|April 11, 2009
PubMed
Summary

Low-energy electrons modify organic films. Xenon coatings enable selective C-H bond breaking at methyl sites via resonant excitation, unlike non-selective subsurface bond rupture.

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Area of Science:

  • Surface Science
  • Materials Chemistry
  • Nanotechnology

Background:

  • Self-assembled monolayers (SAMs) are crucial in organic electronics and surface modification.
  • Understanding electron-induced reactions in organic films is key for developing new materials and processes.

Purpose of the Study:

  • To investigate the effect of low-energy electron injection into xenon-coated alkanethiol SAMs.
  • To explore selective chemical modification of organic films using electron-xenon interactions.

Main Methods:

  • Low-energy electron injection (6-11 eV) into xenon-coated self-assembled alkanethiol monolayers.
  • Analysis of electron-induced C-H bond rupture at different sites within the SAM.
  • Investigation of resonant electronic excitations in xenon adsorbates.

Main Results:

  • At most energies, electrons penetrate the Xe film, causing C-H bond rupture at both methyl and methylene sites.
  • At 7.7 eV, resonant excitation of Xe creates transient anionic states, leading to selective C-H bond dissociation at methyl sites.
  • Anionic excitation transfer to the SAM results in localized reactions, with minimal electron conduction along the alkane chain.

Conclusions:

  • Electronically excited charged state mobility in alkanethiols is limited, less than that of excess electrons.
  • Low-energy electrons can induce highly site-selective chemical modifications in homogeneous organic films.
  • Xenon overlayers offer a pathway to control electron-induced reactions in organic materials.