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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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.
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Preparation and Reactions of Thiols02:33

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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.
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Disulfide-Containing Nitrosoarenes: Synthesis and Insights into Their Self-Polymerization on a Gold Surface.

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Disulfide-containing nitrosoarenes self-polymerize on gold surfaces to form thicker azodioxy thiolate films. These films, unlike nitro derivative monolayers, exhibit island-like structures and influence future surface design.

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Area of Science:

  • Surface Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Nitrosoarenes with disulfide functionalities are novel precursors for surface film formation.
  • Self-polymerization via azodioxy bonds on gold surfaces is a key characteristic.
  • Comparison with analogous nitro derivatives highlights unique properties of nitrosoarene films.

Purpose of the Study:

  • Synthesize and characterize disulfide-containing nitrosoarenes as precursors for azodioxy thiolate films.
  • Investigate the self-polymerization behavior and film formation on Au(111) substrates.
  • Compare the properties of nitrosoarene-derived films with those of nitro-derived films.

Main Methods:

  • Synthesis of nitrosoarene precursors: bis(4-nitrosobenzyl) disulfide (NOBnDS), 4-nitrosophenyl disulfide (NOPDS), and 1,2-bis(4'-nitroso-[1,1'-biphenyl]-4-yl)disulfane (NOBPDS).
  • Solution-phase self-assembly onto Au(111) substrates with varying adsorption times.
  • Characterization using Raman spectroscopy, ellipsometry, water contact angle measurements, AFM, and STM.

Main Results:

  • Raman spectroscopy confirmed the presence of the E-azodioxy group (N═N stretching band) in the films.
  • Ellipsometry indicated thicker films for nitrosoarenes compared to nitro counterparts, suggesting oligomer formation.
  • AFM and STM revealed island-like morphologies and poorly organized surface structures for nitrosoarene films, contrasting with homogeneous nitro derivative monolayers.

Conclusions:

  • Disulfide-containing nitrosoarenes effectively form azodioxy thiolate oligomer films on Au(111).
  • The electronic effects of substituents influence on-surface azodioxide formation.
  • These findings provide insights for designing advanced azodioxy thiolate films on gold surfaces.