T (+98) 23 352 20220
Email: international@du.ac.ir
Damghan University
University Blvd, Damghan, IR
Seied Ali Pourmousavi
Associate Professor of Organic Chemistry
TEL: +98-23-3522-0095
Selected Publications
DOI: 10.1007/s13738-017-1246-2
A series of 4-arylmethylene-3-methylisoxazol-5(4H)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqueous media. Mild conditions, safe, short reaction times, commercially available catalyst, environmentally friendly, no uses of organic solvent and high yields are remarkable advantages to this process. (Z)-4-(3-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one, (HBIM), is characterized by theoretical (density functional theory) and experimental (IR, 1H NMR, CV and UV). The structural parameters, vibrational frequencies, molecular electrostatic potential, frontier molecular orbital analysis (HOMO–LUMO), thermodynamic properties and nonlinear optical properties are found and discussed. UV–Vis spectra are recorded in two organic solvents. Thermal stability of HBIM is studied by thermogravimetric analysis. The molecule orbital contributions are studied using the total and partial density of states (TDOS and PDOS). © 2017, Iranian Chemical Society.
AUTHOR KEYWORDS: Antimony trichloride; DFT calculations; Isoxazol-5(4H)-ones; Spectroscopy; Three-component process
PUBLISHER: Springer Verlag
DOI: 10.1016/j.molstruc.2017.05.010
Sulfonated polynaphthalene (S-PNP) as a carbon-based solid acid efficiently catalyzed the one-pot three-component synthesis of amidoalkyl naphthols. The three-component process of substituted aryl aldehydes, 2-naphthol, and amide (benzamide and acetamide) or urea in the presence of S-PNP under thermal solvent-free conditions is described. Short reaction times, high yields and easy work-up are the advantages of this protocol. Furthermore, the catalyst can be readily recycled and reused without obvious significant loss of activity. Also, density functional theory (DFT) with the aid of M06-2X and B3LYP methods was used for studying of the optimized structure, molecular orbitals, electrostatic potential (ESP) map and spectroscopic analysis of some selected amidoalkyl naphthols. The thermochemical parameters of reactions including enthalpy, internal energy, entropy and Gibbs free energy were also investigated. The theoretically calculated infrared (IR) and 1H nuclear magnetic resonance (NMR) spectra of title compounds were compared to the experimental data. Based on the results, the synthesis of amidoalkyl naphthols is exothermic. A good consistency between the calculated and observed spectral data was found. © 2017 Elsevier B.V.
AUTHOR KEYWORDS: Amidoalkyl naphthols; DFT; Multicomponent reaction; Sulfonated polynaphthalene; Thermochemistry
INDEX KEYWORDS: Amides; Carbon; Catalysts; Density functional theory; Free energy; Gibbs free energy; Molecular orbitals; Naphthol; Nuclear magnetic resonance; Thermochemistry; Urea, Electrostatic potentials; Multi-component reactions; Nuclear magnetic resonance(NMR); Optimized structures; Solvent free conditions; Spectroscopic studies; Sulfonated polynaphthalene; Thermochemical parameters, Spectroscopic analysis
PUBLISHER: Elsevier B.V.
DOI: 10.1016/j.jpcs.2017.03.008
A simple and efficient method has been developed for the synthesis of Quinazolines using SbCl3 as a heterogeneous catalysis at room temperature. This method provides a good pathway for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones derivatives in the terms of excellent yields and short reaction times. Also we studied theoretically and experimentally on 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (PDQ). Using density functional theory (DFT), the tautomerism of PDQ was also studied. Thermal stability of PDQ was studied by thermo gravimetric analysis (TGA). The spectroscopic results and theoretical calculations indicate that the strength of intramolecular hydrogen bonding (IHB) of PDQ is stronger than that in 2-methyl-4-quinolinol (2MQ). The absorption spectra of the PDQ in solvents with different polarity were obtained and the results show that PDQ exists in both keto-amine and enol-imine forms in THF, while it has keto-amine form in other solvents. Theoretical results show that the conductance of the two tautomers (keto-amine and enol-imine) varies greatly, which offers that the potential usage of this molecule is as a molecular device. © 2017 Elsevier Ltd
AUTHOR KEYWORDS: 2,3-Dihydroquinazolin-4(1H)-ones; 2-Aminobenzamide; Catalyst; DFT
INDEX KEYWORDS: Catalysis; Catalysts; Chemical bonds; Gravimetric analysis; Hydrogen bonds; Nitrogen compounds; Thermodynamic stability; Thermogravimetric analysis, 2,3-Dihydroquinazolin-4(1H)-ones; 2-Aminobenzamide; Intramolecular hydrogen bonding; Molecular device; Quinazolines; Short reaction time; Spectroscopic investigations; Theoretical calculations, Density functional theory
PUBLISHER: Elsevier Ltd
DOI: 10.1080/00268976.2017.1287439
The (Z)-4-(phenylamino) pent-3-en-2-one (PAPO) was synthesised applying carbon-based solid acid and described by experimental techniques. Calculated results reveal that its keto-amine form is more stable than its enol-imine form. A relaxed potential energy surface scan has been accomplished based on the optimised geometry of NH tautomeric form to depict the potential energy barrier related to intramolecular proton transfer. The spectroscopic results and theoretical calculations demonstrate that the intramolecular hydrogen bonding strength of PAPO is stronger than that in 4-amino-3-penten-2-one)APO(. In addition, molecular electrostatic potential, total and partial density of stats (TDOS, PDOS) and non-linear optical properties of the compound were studied using same theoretical calculations. Our calculations show that the title molecule has the potential to be used as molecular switch. © 2017 Informa UK Limited, trading as Taylor & Francis Group.
AUTHOR KEYWORDS: DFT; molecular switch; Schiff base; spectroscopic investigation; tautomerism
INDEX KEYWORDS: Carbon; Hydrogen bonds; Isomers; Molecular physics; Optical properties; Quantum chemistry, Intramolecular hydrogen bonding; Intramolecular proton transfer; Molecular electrostatic potentials; Molecular switches; Non-linear optical properties; Schiff-base; Spectroscopic investigations; tautomerism, Potential energy
PUBLISHER: Taylor and Francis Ltd.
DOI: 10.1007/s11164-016-2448-4
A novel carbon-based solid-acid nanocatalyst (Sta-SO3H) was simply prepared for the first time by the thermal treatment of sulfuric acid with starch at 180 °C in a sealed autoclave. The catalytic activities of Sta-SO3H as an efficient and reusable catalyst were investigated by the condensation reaction of aldehyde, amine and β-keto ester for the synthesis of functionalized piperidines under solvent-free conditions at room temperature in good to high yields. Density functional theory calculations were used to study the structure of methyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (MPPC) as well as the thermochemistry of the multicomponent reaction. The theoretically calculated infrared and 1H nuclear magnetic resonance spectra of MPPC were compared to the experimental data. It was found that the synthesis of MPPC is exothermic accompanied by a decrease in entropy, internal energy and Gibbs free energy of reaction. Good consistency between the calculated and observed spectral data was found. Also, Sta-SO3H has been developed for the synthesis of acylals (1,1-diacetate) in high yields through the reaction of aldehydes with acetic anhydride at room temperature under solvent-free conditions. The mild conditions, eco-friendliness, excellent yields, short reaction times and use of an inexpensive and reusable catalyst are important features of this method. © 2016, Springer Science+Business Media Dordrecht.
AUTHOR KEYWORDS: 1,1-Diacetates; DFT; Multicomponent reaction; Piperidine; Thermochemistry
INDEX KEYWORDS: Aldehydes; Carbon; Catalyst activity; Condensation reactions; Free energy; Gibbs free energy; Magnetic resonance spectroscopy; Nanocatalysts; Thermochemistry, 1 ,1-Diacetates; Carbon-based solid acid; Important features; Multi-component reactions; Piperidine; Reusable catalysts; Short reaction time; Solvent free conditions, Density functional theory
PUBLISHER: Springer Netherlands
DOI: 10.1007/s11164-015-2084-4
The present study aimed to determine an efficient and solvent-free method to synthesize 2-methyl-4-quinolinol (2MQ, also known as 4-hydroxy-2-methylquinoline) and includes spectroscopic investigations and computational studies. Molecular geometry and vibrational wavenumbers of 2MQ were investigated using the density functional (DFT/B3LYP) method with 6-311++G(d,p) and 6-311++G(2d,p) basis sets. According to calculations, the keto form of 2MQ is more stable than the annual form, and the dimeric conformation is predicted to be more stable than the monomeric conformations. A detailed analysis of the nature of the hydrogen bonding, using topological parameters such as electronic charge density, Laplacian, kinetic and potential energy density evaluated at the bond critical point, is also presented. The 1H nuclear magnetic resonance chemical shifts of the molecule were calculated by the GIAO method. The molecule orbital contributions were studied by using total (TDOS) and partial (PDOS) density of states. The UV-visible spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were investigated by the time-dependent DFT (TD-DFT) approach. The linear polarizability (α) and the first-order hyperpolarizability (β) values of the investigated molecule were computed using DFT quantum mechanical calculations. The results show that the 2MQ molecule may have a nonlinear optical comportment with non-zero values. The stability and charge delocalization of the molecule was studied by natural bond orbital analysis. In addition, a molecular electrostatic potential map of the title compound was studied for predicting the reactive sites. Local reactivity descriptors, such as Fukui functions, local softness and electrophilicity indices analyses, were studied to determine the reactive sites within the molecule. © 2015 Springer Science+Business Media Dordrecht.
AUTHOR KEYWORDS: 2-Methyl-4-quinolinol; 1H NMR and UV spectra; DFT; FT-IR; Hydrogen bonded dimer; NBO analysis
INDEX KEYWORDS: Chemical bonds; Conformations; Electronic properties; Hydrogen; Hydrogen bonds; Molecules; Nuclear magnetic resonance; Potential energy; Quantum theory; Ultraviolet spectroscopy, 2-Methyl-4-quinolinol; DFT; Hydrogen-bonded dimers; NBO analysis; Nmr and uv spectrum, Dimers
PUBLISHER: Springer Netherlands
DOI: 10.1080/17415993.2014.958751
A straightforward and highly efficient procedure for the thioacetalization of a variety of aldehydes and transthioacetalization of acylals and acetals in good to excellent yields using catalytic amounts of sulfonated polyanthracene (S-PAT) is reported. The reactions were carried out in the presence of 1,2-ethanedithiol and 1,3-propanedithiole at room temperature under solvent-free conditions. Thioacetals were also prepared by the reaction of aromatic ketone and dithiole using S-PAT under reflux conditions in H2O as green solvent. © 2014 Taylor and Francis.
AUTHOR KEYWORDS: acetal; carbonyl compound; sulfonated polyanthracene; thioacetalization; transthioacetalization
PUBLISHER: Taylor and Francis Ltd.
DOI: 10.1007/s00706-011-0664-6
Chemoselective and efficient thioacetalization of a variety of aldehydes was achieved in excellent yields at room temperature using 1,2-ethanedithiol in the presence of catalytic amounts of H 2SO 4-silica. Thioacetals were also prepared by transthioacetalization of acylals and acetals under similar conditions. © Springer-Verlag 2011.
AUTHOR KEYWORDS: Acetal; Acylal; Aldehydes; Chemoselectivity; Solvent free; Thioacetalization; Transthioacetalization
H 2SO 4-Silica efficiently catalyzes the three-component condensation reaction of aldehydes, 1,3-dicarbonyl compounds and urea/thiourea under solvent free conditions to afford the corresponding dihydropyrimidinones and thio-derivatives in high yields. Compared to the classical Biginelli reaction conditions, this new method consistently has the advantage of giving good yields and requiring short reaction times.
AUTHOR KEYWORDS: 1,3-Dicarbonyl compounds; Aldehydes; Biginelli reaction; Dihydropyrimidinone; H 2SO 4-Silica; Solvent free conditions
A rapid and efficient method for the transthioacetalization of acylals (1,1-diacetates) and acyclic and cyclic acetals is described. The reaction was carried out using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide (1 mol%). The yield of the transthioacetalization was high and reaction conditions involve the use of acetonitrile as the solvent at room temperature; isolation is simple and the products are nearly pure.
AUTHOR KEYWORDS: 1,1-Diacetate; 1-Benzyl-4-aza-1- azoniabicyclo [2.2.2]octane tribromide; Acetal; Acylal; Transthioacetalization
DOI: 10.5012/bkcs.2011.32.5.1575
Antimony trichloride(SbCl3) was demonstrated to be an effective catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the corresponding cyanosilylethers in good to excellent yields.
AUTHOR KEYWORDS: Carbonyl compounds; SbCl3; Solvent free conditions; TMSCN; Trimethylsilyl cyanide; Trimethylsilylethers
INDEX KEYWORDS: SbCl3; Solvent free conditions; TMSCN; Trimethylsilyl cyanide; Trimethylsilylethers, Aldehydes; Antimony compounds; Carbonylation; Cyanides; Ketones; Organic compounds, Solvents
DOI: 10.1080/10426500902994312
Benzyl DABCO bromide was found to be an efficient and mild reagent for the reduction of sulfoxides to the corresponding sulfide using sulfuric acid adsorbed silica gel under solvent-free conditions at room temperature.
AUTHOR KEYWORDS: Reduction; Solvent free conditions; Sulfoxide; Sulfuric acid adsorbed silica gel
DOI: 10.3906/kim-0805-45
A variety of aldehydes react with acetic anhydride in the presence of a catalytic amount of H2SO4 -silica to afford the corresponding 1,1-diacetates (acylals) in excellent yields. Ketones are not affected under the reaction conditions. The advantages are the simplicity of the acylation procedure, and the relatively non-toxic nature of the catalyst as well as its easy availability and low cost. © TÜBİTAK.
AUTHOR KEYWORDS: Acylals; Aldehydes; Catalysis; H2 SO4-silica; Solvent-free reactions
Benzyl triethyl ammonium tribromide was prepared by oxidation of bromide ion with HNO3. The resulted tribromide was used as an efficient, regioselective, and recoverable reagent for the bromination of anilines, phenols and anisoles in good to excellent yields at room temperature.
AUTHOR KEYWORDS: Activated aromatic compounds; Anilines; Anisols; Benzyl triethyl ammonium tribromide; Phenols; Regioselective bromination
DOI: 10.5012/bkcs.2008.29.7.1332
Stable crystalline 1-Benzyl-4-aza-1-azonia-bicyclo[2.2.2]octane tribromide (BABOT), can be readily synthesized from the reaction of the corresponding bromide with HNO3 and aqueous KBr. Selective Oxidation of a variety of dialkyl and alkyl Aryl sulfides to the corresponding sulfoxides in high yield was achieved by this reagent in solution (CH3CN/H2O) and solvent free conditions. The reaction proceeds under neutral and mild conditions and can be carried out easily at room temperature with regeneration of BABOT. In this method purification of products is straightforward and no over oxidation to sulfone was noted.
AUTHOR KEYWORDS: 1-Benzyl-4-aza-1-azonia-bicyclo[2. 2.2]octane tribromide; Oxidation; Solvent free; Sulfide; Sulfoxide
INDEX KEYWORDS: Solvents; Sulfur compounds, 1-Benzyl-4-aza-1-azonia-bicyclo[2. 2.2]octane tribromide; Environmentally benign synthesis; Oxidation of sulfides; Selective oxidation; Solvent free; Solvent free conditions; Sulfide; Sulfoxide, Oxidation
PUBLISHER: Korean Chemical Society
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