Related Experiment Video
Updated: May 10, 2026
06:34
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
9H-Carbazole-9-carbo-thioic di-thio-peroxy-anhydride.
Nesimi Uludağ1, Murat Ateş, Nagihan Caylak Delibaş
1Department of Chemistry, Namık Kemal University, 59030 Değirmenaltı, Tekirdağ, Turkey.
Summary
This study reveals the crystal structure of a carbazole compound (C26H16N2S4) with twofold rotational symmetry. Aromatic π-π stacking interactions are observed between adjacent molecules in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Carbazole derivatives are important in organic electronics and materials science.
- Understanding molecular packing and intermolecular interactions is crucial for designing new materials.
Purpose of the Study:
- To determine the crystal structure of the title compound, C26H16N2S4.
- To investigate the molecular symmetry and intermolecular interactions in the solid state.
Main Methods:
- Single crystal X-ray diffraction was used to elucidate the crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular distances was performed.
Main Results:
- The molecule C26H16N2S4 exhibits twofold rotational symmetry.
- The carbazole skeleton is nearly planar, with a maximum deviation of 0.054(5) Å.
- Aromatic π-π stacking was observed between parallel carbazole ring systems, with shortest centroid-centroid distances of 3.948(3) Å and 3.751(3) Å.
Conclusions:
- The crystal structure of C26H16N2S4 is characterized by its high symmetry and planar carbazole core.
- The observed π-π stacking suggests potential for charge transport in related materials.
- This structural information is valuable for the rational design of novel organic semiconductors and functional materials.
More Related Videos
Related Concept Videos
02:33Preparation and Reactions of Thiols
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.
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:07Preparation of Acid Anhydrides
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
02:26Preparation 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.
01:24Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...