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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

Preparation and Reactions of Thiols

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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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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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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,...
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Metal-Ligand Bonds02:51

Metal-Ligand Bonds

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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Bis[1,2-bis-(3,5-di-methyl-phen-yl)ethyl-ene-1,2-di-thiol-ato(1-)]nickel(II).

Titir Das Gupta1, Jackson Guite1, LiWen Hirt1

  • 1Department of Chemistry, Tulane University, 6400 Freret Street, New Orleans, Louisiana 70118-5698, USA.

Acta Crystallographica. Section E, Crystallographic Communications
|June 9, 2025
PubMed
Summary
This summary is machine-generated.

The study reveals a novel nickel complex, [Ni(C18H18S2)2], exhibiting a radical monoanionic ligand state. Its crystal structure shows molecules forming columnar stacks with specific angles and intermolecular hydrogen bonds.

Keywords:
C—H→πarene hydrogen bondscrystal structuredi­thiol­eneelectron-donatingnickel

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Area of Science:

  • Inorganic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Nickel complexes with sulfur-containing ligands are of interest for their electronic and structural properties.
  • Understanding the redox states of ligands is crucial for predicting complex behavior.

Purpose of the Study:

  • To characterize the crystal structure and bonding of the novel nickel complex [Ni(C18H18S2)2].
  • To investigate the ligand's redox state and intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Bond length analysis to determine ligand redox state.
  • Analysis of molecular packing and intermolecular interactions.

Main Results:

  • The compound [Ni(C18H18S2)2] crystallizes in the monoclinic P21/c space group.
  • Intra-ligand bond lengths indicate a radical monoanionic redox level for the di-thiol-ene ligand.
  • Molecules form columnar stacks along the a-axis with specific cant angles and are stabilized by methyl C-H→πarene hydrogen bonds.

Conclusions:

  • The crystal structure provides insights into the coordination environment and electronic state of the nickel complex.
  • The observed molecular stacking and hydrogen bonding influence the solid-state properties of the material.