Academic literature on the topic 'Benzoyl thiourea'

By the reaction of benzoyl chloride, potassium isothiocyanate and the appropriate halogenoaniline, i.e. 2/3/4-(bromo/iodo)aniline, we have obtained five new 1-benzoyl-3-(halogenophenyl)thioureas, namely, 1-benzoyl-3-(2-bromophenyl)thiourea and 1-benzoyl-3-(3-bromophenyl)thiourea, C14H11BrN2OS, and 1-benzoyl-3-(2-iodophenyl)thiourea, 1-benzoyl-3-(3-iodophenyl)thiourea and 1-benzoyl-3-(4-iodophenyl)thiourea, C14H11IN2OS. Structural and conformational features of the compounds have been analyzed using X-ray diffraction and theoretical calculations. The novel compounds were characterized by solid-state IR and 1H/13C NMR spectroscopy. The conformations and intermolecular interactions, such as hydrogen bonds, π–π and S(6)...π stacking, and X...O (X = I or Br), I...S and I...π, have been examined and rationalized, together with four analogous compounds described previously in the literature. The set of nine compounds was chosen to examine how a change of the halogen atom and its position on the phenyl ring affects the molecular and crystal structures.

Thermolysis of N/benzoyl-N’,N’-diphenylthiourea (BDTU)(I) at 250°C gives NH3, H2S, H2O, benzaldehyde, benzil, benzonitrile, diphenylamine, diphenylcyanamide, 2-phenylbenzimidazole, benzoyl isothiocyanate, carbazole and 2-phenylbenzthiazole, whereas, thermolysis of N-benzoyl-N'-o-tolylthiourea (BTTU) (II) under the same conditions afford NH3, H2S, H2O, benzaldehyde, benzil, benzonitrile, o-toluidine, o-tolyl isothiocyanate, o-tolylcyanamide, benzoyl isothiocyanate and N,N’-di-o-tolylthiourea. The main feature of these thermolyses is homolysis of the amide and thioamide bonds providing free radicals that undergo the common reactions involving H-abstraction, dimerization, coupling, fragmentation, rearrangement and cyclization. A suitable mechanism has been suggested to account for the observed products.

A series of novel thiourea and amide liquid crystals containing 5-membered isoxazoline and isoxazole rings were synthetized and the liquid crystal properties studied. Thioureas were obtained using a condensation reaction of benzoyl chlorides, arylamines and ammonium thiocyanate. The amides, on the other hand, were the byproduct of a quantitative reaction which used potassium cyanate as the starting material. Thiourea and amide derivatives were predominantly SmA mesophase inductors. A nematic mesophase was observed only for thioureas and amides containing an isoxazole ring. Additionaly, the liquid crystal behavior was also dependent on the relative position of nitrogen and oxygen atoms on the 5-membered heterocycle.

A nonlinear optical material, 1-benzoyl-3-(4-benzyl)thiourea (C15H14N2OS), has been characterized by X-ray powder diffraction. Experimental values of 2θ corrected for systematic errors, relative peak intensities, values of d, and the Miller indices of 82 observed reflections with 2θ up to 80° are reported. The powder diffraction data have been evaluated, and the figures-of-merit are reported. The least-squares refined unit cell parameters are a=22.0243(6)Å, b=10.9795(7)Å, c=13.0322(8)Å, β=116.88(2)°, V=2810.8(9)Å3, Z=8, Dx=1.278 g/cm3, space group Pn.

New benzoyl thiourea derivatives and their nickel and copper complexes were synthesized. The structure of the synthesized compounds were confirmed by elemental analysis, FT-IR, and1H NMR techniques. Four of the synthesized compounds are analyzed by X-ray single crystal diffraction technique. WhereasN,N-dimethyl-N′-(4-fluorobenzoyl)thiourea,N,N-diethyl-N′-(4-fluorobenzoyl)thiourea, andN,N-di-n-butyl-N′-(4-fluorobenzoyl) thiourea crystallize in the monoclinic system,bis(N,N-di-n-propyl-N′-(4-fluorobenzoyl)thioureato) nickel(II) complex crystallizes in the triclinic system. These ligand molecules form dimers through strong intermolecular hydrogen bonds such as N–H⋯S, C–H⋯O, and N–H⋯O. Moreover, there are different types of intramolecular interactions in the crystal structures.Bis(N,N-dimethyl-N′-(4-fluorobenzoyl)thioureato) nickel(II) complex has a nearly square-planar coordination. The distance of nickel atom from the best plane through the coordination sphere is 0.029 Å.

The reaction of some new Schiff bases ( 2-[(2-Amino – ethylimino)-methyl]-R , 2-({2-[(R-benzylidene)-amino]-ethylimino}-methyl)-R with Benzoyl chloride or Acetyl chloride were carried out. Subsequent reactions of these products N-(2-Amino-ethyl)-N-[Chloro-(R) –methyl]-benzamide or N-(2-{?-[chloro-(R) –methyl]-amino}-ethyl)-N-[chloro-(R) –methyl]- benzamide with thiourea afforded thioureas compounds. The synthesized compounds were confirmed by their IR,UV,spectra and C.H.N. analysis.

The stoichiometric ionization constants ofN,N-dialkyl-N′-(4-substituted benzoyl) thiourea (Substitutes: H, Cl, and Br; alkyl groups: ethyl,n-propyl,n-butyl, and phenyl) derivatives have been determined potentiometrically in dioxane-water (v:v, 50:50) mixture at ionic strength of 0.1 M and25.0±0.1°C. The ionization constants were calculated with the BEST computer program and the formation curves using the data obtained from the potentiometric titrations. The effects of substituents and alkyl groups on the ionization constants of the benzoyl thiourea derivatives have been investigated. A comparison of the basicities of ethyl,n-propyl, andn-butyl thiourea derivatives(−C2H5<−C3H7<−C4H9)shows that then-butyl group is a more powerful electron-releasing group than the other groups in 50% dioxane-50% water mixture (v:v). So, the acidity of benzoyl thiourea derivative compounds decreases, while the length of alkyl chain increases. The orders ofpKavalues for all thiourea derivatives are as expected in the light of steric, resonance and inductive effects of substituents. Furthermore, when the basicities of halogen derivatives of the same substitution pattern are compared, orders obtained (4-Br<4-Cl<4-H) can be explained by considering the total electronic substituent effect (electron-withdrawing and electron-donating effects) except the 4-Br_Ph derivative.

A novel compound N-benzoyl-N＇-(4-chlorobenzamido) thiourea was prepared from benzoyl isothiocyanate which was obtained from benzoyl chloride and potassium thiocyanate, and 4-chlorobenzoyl hydrazine which was obtained from ethyl 4-chlorobenzoate and hydrazine hydrate. IR,1H NMR,13C NMR and elemental analysis were utilized to determine the structure of the thiourea. The biological tests indicated that the target compound had antibacterial activity against bacillus subtilis and taphylo-coccus aurers. Meanwhile, the thermal stability was investigated by thermogrativity（TG） and differential thermogrativity (DTG). The results demonstrated there was one weight-loss in the thermal decomposition process. The thermal kinetics equation obtained describing the thermal decomposition process was expressed as .

xviii, 724 p. : ill. (some col.)
Structural trends applicable to crystal engineering were studied in three classes of thiourea-based compounds. The aim of the study was to identify, predict, and ultimately design reliable single-molecule structural features, which could then be used to engineer crystals with desirable properties. In one class of compounds, this goal was achieved: N-alkyl and N-aryl derivatives of N,N'-bis(3-thioureidopropyl)piperazine adopted an identical conformation in the solid state, which resulted in near-identical crystal packing. A second class of closely related compounds, N-substituted tris(2-thioureidoethyl)amines, showed no such reliability in the solid state, likely because the parent structure lacked hydrogen-bonding functionalities sufficient to control intramolecular structure. In the third class of compounds that we studied, 1-benzoyl-3-(2-pyridyl)thioureas, substitution patterns were often predictive of molecular conformation; however, these intramolecular trends did not lead to recognizable crystal packing motifs. Nevertheless, certain physical properties observed in this last class of compounds--color, solubility, and often crystallinity--were conformer-specific, interestingly without any apparent relevance to crystal lattice structure. Solution-state and solid-state conformational trends in these 1-benzoyl-3-(2-pyridyl)thioureas have been documented, and speculations as to the source of color in one of the two observed conformations have been noted.
Committee in charge: Shih-Yuan Liu, Chairperson; Kenneth M. Doxsee, Advisor; Michael M. Haley, Member; Catherine J. Page, Member; Paul J. Wallace, Outside Member

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Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES
In this work six asymmetric thyourea, derived from benzylamine and phenethylamine, were synthesized by reaction of p-substituted phenyl isothiocyanates in the presence of benzylamine and phenethylamine in toluene as solvent by irradiation in ultrasonic bath, featuring the first report in the literature of the adoption of this method for such molecules. The compounds were obtained in high purity, requiring only one recrystallization from hexane/dichloromethane. Yields were very satisfactory, ranging from 89 to 98%. The compounds were characterized by spectroscopic techniques such as 1H, 13C Nuclear Magnetic Resonance and IR. The synthesized compounds were evaluated by electrochemical potentiodynamic polarization techniques, Electrochemical Impedance Spectroscopy and Linear Polarization Resistance as inhibitors to the corrosion AISI 1020 carbon steel in 1M HCl media. Molecular modeling was used for better visualization of the thiourea structures and to correlate theoretical parameters such as the energy of the symmetrical frontier orbital, Mulliken charge on the sulfur atom and dipole moment with the experimental results for corrosion efficiency. In general, all compounds showed corrosion inhibition efficiency with characteristics of mixed inhibitors with anodic trend, however compounds with nitro substituent showed less efficiency, a fact that may be related to their electrons withdrawing potential, which consequently decreases the electron density at the possible center of chemical adsorption, the sulfur atom. However, compounds which showed no substituent and those that contain electron donating group (OCH3) stood out as inhibitors, highlighting N- (p-methoxyphenyl) -N'-phenetylthiourea, which showed 95% efficiency corrosion inhibition, from Electrochemical Impedance spectroscopy. Thus, the asymmetric thiourea benzyl and phenethyl-substituted, especially methoxy-substituted phenyl, can be considered as promising corrosion inhibitors for carbon steel in acid.
Nesse trabalho de disserta??o foram sintetizadas seis tioureias assim?tricas, derivadas da benzilamina e fenetilamina. A obten??o ocorreu atrav?s da rea??o dos isotiocianatos de fenila p-substituidos na presen?a da benzilamina e fenetilamina em tolueno como solvente atrav?s de irradia??o em banho de ultrassom, sendo o primeiro relato na literatura dessa metodologia para tais mol?culas. Os compostos foram obtidos em alto grau de pureza, sendo necess?ria apenas uma recristaliza??o em hexano/diclorometano. Os rendimentos foram muitos satisfat?rios, variando de 89 ? 98%. Os compostos foram caracterizados por t?cnicas espectrosc?picas como Resson?ncia Magn?tica Nuclear 1H,13C e Infravermelho. Os compostos sintetizados foram avaliados atrav?s das t?cnicas eletroqu?micas de Polariza??o Potenciodin?mica, Espectroscopia de Imped?ncia Eletroqu?mica e Resist?ncia a Polariza??o Linear quanto ? a??o como inibidores de corros?o frente a a?o carbono AISI 1020 em HCl 1 mol.L-1. A Modelagem Molecular foi utilizada para melhor visualiza??o das estruturas das tioureias e correlacionar os par?metros te?ricos como a energia dos orbitais de fronteiras sim?tricos, carga de Mulliken no ?tomo de enxofre e momento dipolar com os resultados experimentais da efici?ncia anticorrosiva. De forma geral, todos apresentaram efici?ncia de inibi??o ? corros?o com caracter?sticas de inibidores mistos com tend?ncia an?dica, por?m os compostos com substituinte nitro apresentaram menor efici?ncia, fato esse que pode estar relacionado ao seu poder retirador de el?trons, que consequentemente, diminui a densidade eletr?nica no poss?vel centro de adsor??o qu?mica, o enxofre. Por?m, os compostos que n?o apresentaram substituintes e os que cont?m grupo doador de el?trons (OCH3) se destacaram como inibidores, dando destaque a N-(p-metoxi-fenil)-N?-fenetiltioureia, que apresentou efici?ncia de 95% de inibi??o da corros?o, pela t?cnica de Espectroscopia de Imped?ncia Eletroqu?mica. Assim, as tioureias assim?tricas benzil e fenetil-substitu?das, especialmente met?xi-fenil substitu?das, podem ser consideradas como promissores agentes inibidores da corros?o para o a?o-carbono em meio ?cido.

Although natural amino acids are readily available, there is a continuing need for unnatural amino acids. Jon C. Antilla of the University of South Florida has described (J. Am. Chem. Soc. 2007, 129, 5830) a promising approach, based on the enantioselective organocatalytic reduction of imines such as 1 derived from α-keto esters. The aryl group is easily removed to give the primary amine. Mukund P. Sibi of North Dakota State University has developed (J. Am. Chem. Soc. 2007, 129, 4522) an enantioselective Mg catalyst that mediated the addition of benzyl hydrazine 6 to imides such as 5. The initial adduct cyclized to the pyrazolidinone 7. Karl Anker Jørgensen of Aarhus University has reported (Angew. Chem. Int. Ed. 2007, 46, 1983) a complementary protocol for the enantioselective conjugate addition of a nitrogen nucleophile. Enantioselective homologation can also be a powerful approach. Benjamin List of the Max-Planck-Institute, Mülheim has found (Angew. Chem. Int. Ed. 2007, 46, 612; Organic Lett. 2007, 9, 1149) that three-component coupling of acetyl cyanide, an aldehyde and benzylamine under the influence of the Jacobsen thiourea catalyst 10 delivered the onecarbon homologated nitrile 12 in high ee. Other homologation methods are also effective. Li Deng of Brandeis University has shown (Organic Lett. 2007, 9, 603) that under the influence of cinchona-derived quaternary salts, malonates will add to racemic amido sulfones such as 13 to give the β-amino malonate 14 in high ee. Fujie Tanaka and Carlos F. Barbas III of Scripps/La Jolla have found (Angew. Chem. Int. Ed. 2007, 46, 1878) that the simple organocatalyst proline will mediate the aza-Baylis Hillman addition of an unsaturated aldehyde such as 15 to 16 in high ee. The alkene 17 is the kinetic product. On prolonged exposure to the reaction conditions, 17 was equilibrated to the more stable 18 . Ming-Hua Xu and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry have established (J. Am. Chem. Soc. 2007, 129, 5336) a robust protocol for the enantioselective assembly of -arylated benzylamines such as 21.