59104-31-3

Usage

Type of compound

Thiourea derivative

Applications

a. Catalyst in organic synthesis
b. Inhibitor of various enzymes
c. Anti-fungal and anti-microbial properties
d. Potential use in treating diseases
e. Reagent in the preparation of other organic compounds

Significance

Important and versatile chemical in the field of organic chemistry

Upstream product

• 75-15-0 carbon disulfide 
• 108-69-0 3,5-dimethylaminoaniline 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 1227513-27-0 N,N',N''-tri(3,5-xylyl)guanidine 
• 1404310-24-2 C₁₇H₂₀N₂S*C₅H₈O₂ 
• 42171-16-4 1,3-bis(3,5-dimethylphenyl)carbodiimide 

Relevant academic research and scientific papers

Hydrogen-bonding thiourea organocatalysts: The privileged 3,5-bis(trifluoromethyl)phenyl group

We present evidence that the privileged use of the 3,5-bis(trifluoromethyl) phenyl group in thiourea organocatalysis is due to the involvement of the ortho-CH bond in the binding event with Lewis-basic sites. We utilized a combination of low-temperature IR spectroscopy, 2D NMR spectroscopy, nano-MS (ESI) investigations, as well as density functional theory computations [M06/6-31+G(d,p), including solvent corrections as well as natural bond orbital and atoms-in-molecules analyses] to support our conclusions that bear implications for catalyst design. The present work reveals that thiourea derivatives bearing a 3,5-bis(trifluoromethyl)phenyl group interact with Lewis basic sites of carbonyl derivatives through NH and highly polarized ortho-CH interactions in hydrogen-bonded complexes. Evidence is provided through a combination of DFT, variable-temperature IR and NMR spectroscopy, as well as MS (ESI) studies.

Synthesis and conformational features of sym N,N′,N″- triarylguanidines

A one pot reaction involving sym N,N′-diarylthiourea and the respective arylamine in the presence of aq. KOH in nitrobenzene at ≥105°C afforded sym N,N′,N″-triarylguanidine in fair to good yield and the products have been characterized. Sym N,N′,N″-tri(4-tolyl)guanidine possesses (7) anti-anti conformation, sym N,N′,N″-tri(2-tolyl) guanidine (8) and sym N,N′,N″-tris(2,4-xylyl)guanidine (11) each possess anti-anti αβα conformation whereas sym N,N′,N″-tris(2-anisyl)guanidine possesses (9) syn-anti αββ conformation as determined by single crystal X-ray diffraction data. The observed conformations appear to result from a subtle balance between steric factor associated with the aryl substituent and multiple electronic factors namely n-π conjugation/negative hyperconjugation and non-covalent interactions in the crystal lattice. Indian Academy of Sciences.