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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

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, similar...

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.

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Chirality at Nitrogen, Phosphorus, and Sulfur

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

Hybridization of Atomic Orbitals II

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1,2-Bis(4-ethynylphen-yl)disulfane.

Qi Xiao¹, Rui Liu, Yu-Hao Li

¹Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a C(16)H(10)S(2) compound, revealing near-planar sulfur atoms and a significant dihedral angle between benzene rings. Intramolecular interactions and π-π stacking influence molecular arrangement in the solid state.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding molecular geometry and intermolecular forces is crucial for predicting material properties.
Sulfur-containing organic compounds exhibit diverse electronic and structural characteristics.
Crystal packing influences bulk properties and reactivity.

Purpose of the Study:

To elucidate the detailed crystal structure of the title compound C(16)H(10)S(2).
To investigate the spatial arrangement of sulfur atoms and benzene rings.
To identify and characterize intramolecular and intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
Analysis of atomic coordinates and bond lengths/angles provided geometric insights.
Intermolecular interaction analysis, including hydrogen bonding and π-π stacking, was performed.

Main Results:

The sulfur atoms exhibit near-planarity with their bonded benzene rings (deviations of 0.092(1) and 0.022(1) Å).
A substantial dihedral angle of 79.17(3)° was observed between the two benzene rings.
An intramolecular C-H⋯S hydrogen bond forms a five-membered ring, and molecules stack along the a-axis with π-π interactions at 3.622(10) Å.

Conclusions:

The crystal structure is characterized by specific geometric constraints and stabilizing intramolecular interactions.
The observed π-π stacking suggests potential for electronic interactions in the solid state.
This structural data provides a foundation for further studies on the compound's physical and chemical properties.