Synthesis of Meso-tetraarylporphyrins and in Situ Producing the Valuable Nanoparticles as a Byproduct: Potential Application in Solar Cells
Neda
Attaran
Department of Medical Nanotechnology, Applied Biophotonics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran
author
Hossein
Eshghi
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad
author
text
article
2021
eng
Meso-Tetraarylporphyrins are synthesized from pyrrole and aryl aldehydes cleanly and efficiently using an equimolar amount of Cr(HSO4)3 in the presence of chloranil as oxidant. Also, for the first time, meso-tetraphenylporphyrinogen is oxidized by HAuCl4 to obtain meso-tetraphenylporphyrin and valuable gold nanoparticles as byproduct, in good yield. Transmission electron microscopy (TEM) analysis indicated that spherical gold nanoparticles in the 25 diameter were obtained in the presence of meso-tetraphenylporphyrinogen at room temperature without using any capping agents. The Fourier transform infrared spectroscopy (FT-IR) supports the presence of tetraphenylporphyrin dye molecules on the surface of gold nanoparticles. These obtained gold nanoparticles could be used for various unknown and known applications, especially for designing efficient dye sensitized solar cells, selective catalysts and photodynamic therapy agents.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
1
11
https://www.orgchemres.org/article_130601_73033757396acc615b84d7fef50adfef.pdf
dx.doi.org/10.22036/org.chem.2021.239823.1248
Effects of Substituent and Temperature on the Electronic Properties and Thermodynamics Parameters of 1-(Benzothiazolylamino) Methyl-2-Naphthol: A Computational Study
Zohreh
Khanjari
Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
author
Bita
Mohtat
Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
author
Reza
Ghiasi
Department of Chemistry, Faculty of science, East Tehran Branch, Islamic Azad University, Tehran, IRAN.
author
Hoorieh
Djahaniani
Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran
author
Farahnaz
Kargar Behbahani
Department of Chemistry, Karaj branch, Islamic Azad University, Karaj, Iran.
author
text
article
2021
eng
The effects of substituent and temperature on the 1- (benzothiazolylamino) methyl - 2- naphthol molecules were studied at CAM-B3LYP/6-311G (d,p) level of theory. Selected substitutions were NH2, OH, Me, F, Cl, CHO, COOH, CN and NO2. Substituent effect on the frontier orbitals energies, HOMO-LUMO gap, chemical potential, and electrophilicity were explored. Dependencies of energy changes, reactivity properties and thermodynamics parameters (G, H and S) on the Hammett's constants (p) were provided. Thermodynamics parameters values of the formation reaction were studied reaction at 100-1000 K range. Computational investigation of the substituents and temperature influences on the formation reaction of the 1-(benzothiazolylamino) methyl-2-naphthol showed the negative E values in the studied reactions. Calculated dipole moment values reveal the presence of the EWGs induced a larger dipole moment compared with the EDGs. Higher negative values were found in the presence of EWGs compared to EDGs. Frontier orbitals were stabilized in the presence of EWGs. However, frontier orbitals were destabilized in the presence of EDGs. Thermodynamic analysis revealed that these reactions were non-spontaneous and exothermic. The G and negative H values were increased with increasing the temperature. Optimization and vibrational analysis were done with Gaussian 09 software package. The standard 6-311G(d,p) basis set was considered for the elements, respectively. CAM-B3LYP functional was used for the optimization of the geometries of the compound . This functional is Handy and coworkers’ long range corrected version of B3LYP using the Coulomb-attenuating method The identities of the optimized structures as an energy minimum were confirmed by vibrational analysis
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
12
22
https://www.orgchemres.org/article_131516_dd94dfdb138b6e4af46977bb0cf6f67b.pdf
dx.doi.org/10.22036/org.chem.2021.245120.1254
Nano-Fe3O4/TiCl2/cellulose as an Efficient and Ggreen Magnetic Nanocatalyst for the Synthesis of 2,3-Dihydro-2-substituted-1H-naphtho[1,2-e][1,3]oxazine Derivatives
Sara
Azad
Department of Chemistry, Yazd University, Yazd, Iran
author
Bi Bi Fatemeh
Mirjalili
Department of Chemistry, Yazd University, Yazd, Iran
author
Abdolhamid
Bamoniri
Departent of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran
author
text
article
2021
eng
Nano-Fe3O4/TiCl2/cellulose as a green and recyclable nanocatalyst was synthesized and characterized by FT-IR, FESEM, TEM, XRF, BET, VSM, EDX and XRD. The prepared magnetic nanocatalyst was applied for the synthesis of 2,3-dihydro-2-substituted-1H-naphtho[1,2-e][1,3]oxazine under room temperature grinding condition. Short reaction time, high yield, green media, easy work-up, simple magnetic recovery and reusability of the catalyst are the important features of the present protocol.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
23
31
https://www.orgchemres.org/article_133334_f42b513fb7e12dee79d0d0a8a8ef3375.pdf
dx.doi.org/10.22036/org.chem.2021.252146.1256
Old Drugs for a Newly Emerging Viral Disease, COVID-19: Bioinformatic Prospective
Mohammad Reza
Dayer
Department of Biology, Faculty of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran
author
text
article
2021
eng
The COVID-19 outbreak caused by the SARS-CoV-2 virus in late 2019 and early 2020 comprises a serious pandemic threat worldwide. Given the severity of the disease and the fact that there is no approved cure for this infectious disease, it seems reasonable to search for better candidates' drugs among approved antiviral or even antibacterial drugs for their anti-COVID-19 capability in contrast to the currently approved drugs. The enzyme main protease of SARS-CoV-2 that plays an important role in the virus life cycle seems to be a good target for inhibition by drugs. Accordingly, in the present work by using the molecular docking method we used the newly released coordinate structure of the protease as a target and 40 approved drugs from anti-viral, anti-parasite anti-malaria groups as ligands for docking experiments. Blind and active site-directed docking experiments were carried out on the optimized and equilibrated structure of protease at pH 7, 37 degrees centigrade of temperature, and 1 atmosphere of pressure. Our results indicate that based on binding energy, percent of binding site occupation, membrane transportability, and the maximum allowed dosage, erythromycin, clarithromycin, Amprenavir, Darunavir, Cefixime, and Tetracycline are among the enrolled drugs merit best parameters for clinical evaluation and their therapeutic potential in COVID-19 outbreak.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
32
41
https://www.orgchemres.org/article_135739_195bcd99e3453b58d249de043d2ea60b.pdf
dx.doi.org/10.22036/org.chem.2021.240124.1250
Sonosynthesis of Thiazolidinones Using Nano-Fe3O4-tethered Polyhedral Oligomeric Silsesquioxanes with Eight Branches of 3-Aminopropyltriethoxysilane
Javad
Safaei-Ghomi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P. O. Box: 87317-51167, I. R.Iran
author
Seyed Hadi
Nazemzadeh
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P. O. Box: 87317-51167, I. R.Iran
author
Mohammed
Alnasrawi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P. O. Box: 87317-51167, I. R.Iran
author
Hossein
Shahbazi-Alavi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P. O. Box: 87317-51167, I. R.Iran
author
text
article
2021
eng
An effective way for the synthesis of bis-thiazolidinones was applied by one-pot pseudo-five-component reaction of benzaldehydes, ethylenediamine, 2-mercaptoacetic acid with nano-Fe3O4-tethered polyhedral oligomeric silsesquioxanes with eight branches as catalyst under ultrasonic conditions. The catalyst has been characterized by FT-IR (Fourier-transform infrared spectroscopy), SEM (scanning electron microscope), XRD (X-ray diffraction), EDS (Energy-dispersive X-ray spectroscopy), BET (Brunauer-Emmett-Teller), TGA (Thermogravimetric analysis) and VSM (vibrating-sample magnetometer). The remarkable advantages of this methodology are easy work-up, short reaction times, high to excellent product yields, low catalyst loading and reusability of the catalyst.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
42
53
https://www.orgchemres.org/article_141375_b1f20a333cec941164ecbf873a64175d.pdf
dx.doi.org/10.22036/org.chem.2020.230206.1244
Catalyst-free Preparation of 4H-1,3,4-Oxadiazines in H2O
Sedighe
Mozafari Vanani
Department of Chemistry, College of Science, Yazd University, P. O. Box: 89195-741, Yazd, Iran
author
Mohammad Ali
Amrollahi
Department of Chemistry, College of Science, Yazd University, P. O. Box: 89195-741, Yazd, Iran
author
text
article
2021
eng
This report provides a description of a novel and efficient procedure for the synthesis of substituted 4H-1,3,4-oxadiazines via reaction of various vinyl cyanides and acetohydrazide in H2O under catalyst-free conditions. The remarkable advantages are the simplicity of the experimental procedures, high yields, and avoidance of organic solvents. Products were characterized by melting point, IR, 1H- and 13C-NMR spectra, and elemental analysis. The desired products were obtained in >85% yields.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
54
60
https://www.orgchemres.org/article_141377_93da2be194e0278c630af50b13816a87.pdf
dx.doi.org/10.22036/org.chem.2021.255031.1257
An Investigation on the QSAR Modeling of Carfilzomib Derivatives Using Monte Carlo Method and Novel Modelling-optimization Approach
Robabeh
Sayyadi Kord Abadi
Department of Chemistry and Chemical Engineering, Rasht Branch, Islamic Azad University, Rasht, Iran
author
Omid
Alizadeh
Department of Chemistry and Chemical Engineering, Rasht Branch, Islamic Azad University, Rasht, Iran
author
Ghasem
Ghasemi
Department of Chemistry and Chemical Engineering, Rasht Branch, Islamic Azad University, Rasht, Iran
author
text
article
2021
eng
The activity of the 25 different Carfilzomib derivatives was estimated using multiple linear regression (MLR), artificial neural network (ANN), and genetic algorithm(GA) and simulated annealing algorithm (SA) and Imperialist Competitive Algorithm (ICA) as optimization methods. The obtained results from MLR-MLR, MLR-GA, SA-ANN and GA-ANN techniques were compared and for combinations of modelling-optimization methods observed root mean sum square errors (RMSE) of 0.290, 0.0482, 0.0294, 0.0098 in gas phase, respectively (N=25).A high predictive ability was observed for the MLR-ICA model with the best number of empires/ imperialists (nEmp=50 ) and nEmp=100 with root-mean-sum-squared error (RMSE) of 0.00996 in gas phase. From the MLR-ICA method, it was revealed that RDF 075m, MATS1m, F04[N-O], O-059, F09[C-O] and Mor21p are the most important descriptors. From Monte Carlo simulations, it was found that the presence of double, absence of halogens, oxygen connected to double bond, sp2 carbon connected to double bond, double bond with ring, branching, nitrogen are the most important molecular features affecting the biological activity of the drug. It was concluded that simultaneous utilization of MLR-ICA, GA-ANN and Monte Carlo method can lead to a more comprehensive understanding of the relation between physico-chemical, structural or theoretical molecular descriptors of drugs to their biological activities and facilitate designing of new drugs.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
61
76
https://www.orgchemres.org/article_171801_074be87ee66f2aa25957054bace90b25.pdf
dx.doi.org/10.22036/org.chem.2022.297270.1261
Pd(OAc)2/1,1′-Methylene-3,3′-bis[(N-(isopropyl)imidazol-2-ylidene]: An Efficient Catalyst for the Heck Arylation of Various Olefins
Marzieh
Daryanavard
Estahban Higher Education Center-Shiraz University, Estahban, Iran
author
Behzad
Mohammadi
Department of Inorganic Chemistry, Faculty of Chemistry, Razi University, Kermanshah, 67149, Iran
author
Shirin
Nadri
Department of Inorganic Chemistry, Faculty of Chemistry, Razi University, Kermanshah, 67149, Iran
author
Mohammad
Joshaghani
Department of Inorganic Chemistry, Faculty of Chemistry, Razi University, Kermanshah, 67149, Iran
author
text
article
2021
eng
The Mizoroki-Heck coupling reaction has been carried out using Pd(OAc)2 and bisimidazolium (1,1′-methylene-3,3′-bis[(N-(isopropyl)imidazol-2-ylidene]dibromide) for aryl bromides as well as less reactive chlorobenzene with mono- and di-substituted olefins. Only 0.025 mol% of Pd(II) shows a high activity toward the coupling reaction with turnover number (TON) ≈ 600-3960. Further, this catalyst system, Pd(OAc)2/Bisimidazolium, exhibits the excellent selectivity for the trans-isomer coupling products and the terminal arylation coupling products for mono- and di-substituted olefins, respectively. The nature of olefins (n-butyl acrylate, styrene, and 1,1-disubstituted olefins) has a significant contribution on the yield of the coupling products.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
77
85
https://www.orgchemres.org/article_173368_d7679192153986ebd04b1873a8830051.pdf
dx.doi.org/10.22036/org.chem.2023.360237.1279
A Facile and Green Approach for One-Pot Synthesis of New Pyrrole Derivatives by Three-Component Reaction Between Pyrrole, Arylglyoxals and Meldrum's Acid
Zahra
Damanzan
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan 7718897111, Iran
author
Mohammad
Anary-Abbasinejad
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan 7718897111, Iran
author
Mozhgan
Masoudi
Department of Chemistry, Islamic Azad University, Rafsanjan Branch, Rafsanjan, Iran
author
text
article
2021
eng
An efficient one-pot three-component reaction of pyrrole with arylglyoxal derivatives and Meldrum’s acid (MA) in water at room temperature afforded 2,2-dimethyl-5- (2-oxo-2-aryl-1- (1H-pyrrol-2-yl) ethyl) -1,3-dioxane-4,6-dione derivatives under catalyst-free conditions in high yields. Products were isolated and purified by simple filtration and washing with diethyl ether and their structures were established from their IR and NMR spectroscopic data.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
86
91
https://www.orgchemres.org/article_173379_38175ee40b7180b460b8b842858e05e7.pdf
dx.doi.org/10.22036/org.chem.2023.299025.1263
Review on Oxidative and Reductive Mannich Reaction
Hossein
Eshghi
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 91775-1436, Mashhad, Iran
author
Aida
Mansoori
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 91775-1436, Mashhad, Iran
author
text
article
2021
eng
The development of diastereoselective, catalytic methodologies for synthesis of Mannich products presents specific promise for synthetic applications. Only highly reactive aldehydes such as formaldehyde and acetaldehyde, secondary amine, have been ruled out of the classical Mannich reaction. Highly stereoselective Mannich reactions have been extensively studied and reported. The most powerful enantioselective and diastereoselective C-C bond forming reactions include the asymmetric Mannich reaction such as oxidative and reductive Mannich-reaction. In oxidative type, an oxidizing agent such as oxygen, air, etc. is used. Whereas in reductive Mannich reaction, a reducing agent produces enolate for the generation of a reactive iminium ion. Cross-dehydrogenative coupling reactions (CDC) are a method for generating more complex amines from simpler materials by oxidatively functionalizing amine -CH bonds. Besides, the redox-Mannich reaction uses the same raw materials but includes an isomerization step that makes it simple to create ring-substituted -amino ketones. In this review article, we have tried to study the research that has been done in recent years for oxidative and reductive Mannich reactions.
Organic Chemistry Research
Iranian Chemical Society
2383-242X
7
v.
1
no.
2021
92
108
https://www.orgchemres.org/article_173380_d3098260f833805c62ab5c3b930dc282.pdf
dx.doi.org/10.22036/org.chem.2023.396842.1285