Related Experiment Video
Updated: Jun 5, 2026
08:51
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Benzyl 3-[(E)-benzyl-idene]dithio-carbazate
Shang Shan1, Yu-Liang Tian, Shan-Heng Wang
1College of Chemical Engineering and Materials Science, Zhejiang University of Technology, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
Researchers synthesized a new compound, C(15)H(14)N(2)S(2), via a condensation reaction. The crystal structure reveals an E configuration and intermolecular N-H⋯S hydrogen bonding forming dimers.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Benzyl dithio-carbazate and benzaldehyde are key precursors in organic synthesis.
- Understanding molecular configurations and intermolecular interactions is crucial in chemical research.
Purpose of the Study:
- To synthesize and characterize the crystal structure of a novel compound formed from benzyl dithio-carbazate and benzaldehyde.
- To investigate the molecular geometry and intermolecular interactions within the crystal lattice.
Main Methods:
- Condensation reaction between benzyl dithio-carbazate and benzaldehyde.
- Single crystal X-ray diffraction analysis to determine the crystal structure.
- Analysis of molecular conformation and intermolecular hydrogen bonding.
Main Results:
- Successful synthesis of the title compound C(15)H(14)N(2)S(2).
- The molecule exhibits an E configuration around the N=C double bond.
- A dihedral angle of 84.60(5)° was observed between the phenyl ring and the dithio-carbazate plane.
- Intermolecular N-H⋯S hydrogen bonds were identified, leading to the formation of centrosymmetric supramolecular dimers.
Conclusions:
- The study elucidates the detailed crystal structure of the synthesized compound.
- The observed intermolecular hydrogen bonding plays a significant role in the self-assembly of the molecules into dimers.
- This research contributes to the understanding of structure-property relationships in organic crystals.
Related Concept Videos
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
01:22Electrophilic Aromatic Substitution: Sulfonation of Benzene
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
01:07Structure of Benzene: Kekulé Model
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
01:15Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
01:18Directing and Steric Effects in Disubstituted Benzene Derivatives
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...