Related Experiment Video
Updated: May 19, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
4-(Diphenyl-amino)-benzaldehyde 4-phenyl-thio-semicarbazone
Rafael Mendoza-Meroño1, Laura Menéndez-Taboada, Santiago García-Granda
1Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo - CINN, C/ Julián Clavería, 8, 33006 Oviedo, Spain.
Abstract:
The title mol-ecule, C(26)H(22)N(4)S, is composed of three main parts, viz. a triphenyl-amine group is connected to a phenyl ring by a thio-semicarbazone moiety. The C= N double bond has an E conformation. The crystal packing is dominated by strong hydrogen bonds through the thio-semicarbazone moiety, with pairs of N-H⋯S hydrogen bonds linking the mol-ecules to form inversion dimers with an R(2) (2)(8) ring motif. An intra-molecular N-H⋯N hydrogen bond is also present, generating an S(5) ring motif. Although the structure contains four phenyl rings, π-π stacking inter-actions are not formed between them, probably due to the conformation adopted by the triphenyl-amine group. However, a weak π-π stacking inter-action is observed between the phenyl ring and the delocalized thio-semicarbazone moiety.
Related Concept Videos
Preparation and Reactions of Sulfides
Nucleophilic Aromatic Substitution: Elimination–Addition
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nomenclature of Aromatic Compounds with a Single Substituent
Electrophilic Aromatic Substitution: Sulfonation of Benzene
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
