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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

8.0K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
8.0K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

6.0K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
6.0K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

6.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
6.0K
Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

993
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...
993
Enolate Mechanism Conventions01:15

Enolate Mechanism Conventions

3.2K
When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as...
3.2K
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

1.6K
In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Related Experiment Video

Updated: Apr 15, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

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Thiolate versus Selenolate: Structure, Stability, and Charge Transfer Properties.

Jakub Ossowski1, Tobias Wächter2, Laura Silies3

  • 1†Smoluchowski Institute of Physics, Jagiellonian University, Reymonta 4, 30-059 Krakow, Poland.

ACS Nano
|April 11, 2015
PubMed
Summary
This summary is machine-generated.

Selenolates form stronger bonds with gold substrates than thiolates, yet both self-assembled monolayers (SAMs) exhibit similar charge transfer properties due to electron density redistribution.

Keywords:
bond strengthcharge transfermetal surfacesselenolateself-assembled monolayersself-assembly

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Area of Science:

  • Surface science
  • Nanotechnology
  • Materials chemistry

Background:

  • Self-assembled monolayers (SAMs) are crucial for surface functionalization.
  • Selenolate is explored as an alternative to thiolate headgroups for SAMs on metal surfaces.
  • Debate exists regarding the energetic and charge transport advantages of selenolate vs. thiolate anchor groups.

Purpose of the Study:

  • To resolve controversies surrounding the use of selenolate versus thiolate headgroups in SAMs.
  • To compare the structural, bonding, and charge transfer properties of 6-cyanonaphthalene-2-thiolate and -selenolate SAMs on Au(111).

Main Methods:

  • Fabrication and characterization of 6-cyanonaphthalene-2-thiolate and -selenolate SAMs on Au(111).
  • Competitive exchange and ion-beam-induced desorption experiments to assess headgroup-substrate bonding strength.
  • Core-hole-clock approach to determine dynamic charge transfer properties.

Main Results:

  • Selenolate SAMs exhibit slightly different structural arrangements, indicating better SAM-building ability.
  • Both thiolate and selenolate SAMs show similar packing densities and molecular orientations.
  • Selenolates bind more strongly to the Au(111) substrate than thiolates.
  • Despite bonding differences, charge transfer properties are nearly identical for both SAM types.

Conclusions:

  • Selenolate headgroups offer stronger substrate adhesion compared to thiolates.
  • Electron density redistribution along the molecule compensates for bonding strength differences, leading to similar charge transfer.
  • Both thiolate and selenolate SAMs are viable for applications requiring controlled surface modification and charge transport.