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Related Concept Videos

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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of Amines

In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is broad and...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

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Related Experiment Video

Updated: Jun 24, 2026

Atomically Traceable Nanostructure Fabrication
12:35

Atomically Traceable Nanostructure Fabrication

Published on: July 17, 2015

H-atom position as pattern-determining factor in arenethiol films.

Ki-Young Kwon1, Greg Pawin, Kin L Wong

  • 1Pierce Hall/Department of Chemistry, University of California-Riverside, Riverside, California 92521, USA.

Journal of the American Chemical Society
|April 1, 2009
PubMed
Summary
This summary is machine-generated.

Arenethiol molecules form specific patterns on surfaces, driven by hydrogen bonds. Optimizing intermolecular interactions at key positions guides the design of arenethiol films for advanced applications.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Surface Science
  • Materials Chemistry
  • Supramolecular Chemistry

Background:

  • Arenethiol molecules are crucial for self-assembled monolayers on metal surfaces.
  • Understanding intermolecular interactions is key to controlling film formation and properties.

Purpose of the Study:

  • To investigate the role of hydrogen bonding in the self-assembly of benzenethiol and anthracenethiol derivatives on Cu(111).
  • To establish a general principle for designing arenethiol films based on specific intermolecular interactions.

Main Methods:

  • Low-energy electron diffraction (LEED) and scanning tunneling microscopy (STM) were used to study molecular ordering.
  • Annealing experiments were performed to observe the evolution of molecular arrangements.

Main Results:

  • Benzenethiol (BT) on Cu(111) exhibits S...H hydrogen bonds involving ortho-hydrogens at low coverages.
  • (Methylated) anthracenethiols form rows and patterns, dominated by interactions of terminal aromatic hydrogens.
  • Specific hydrogen atom positions dictate the observed molecular ordering and film formation.

Conclusions:

  • Pattern formation in arenethiols is governed by the optimization of intermolecular interactions at a specific hydrogen atom position on the arene.
  • This principle can guide the rational design of ordered arenethiol films with tailored properties.