Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2264452
In this study, a new deep eutectic mixture (DEM) was prepared from D-fructose, L-arginine, and urea and characterized by Fourier transform infrared (FT-IR), refractive index measurement, and thermogravimetric analysis (TGA). In continue this mixture was used as a green catalyst to promote the synthesis of three important derivatives of heterocyclic compounds. The highlights of this work include some notable advantages such as ease of the preparation and simple catalytic process, low cost, green reaction conditions, biodegradability of the catalyst, short reaction times, high yields of the products and simple work-up. Also, the catalyst could be recovered easily and reused up to several times without significant loss of catalytic activity.
{"title":"Use of a New Natural Deep Eutectic Mixture for the Acceleration of Some of the Important Multi-Component Reactions","authors":"","doi":"10.1080/10406638.2023.2264452","DOIUrl":"10.1080/10406638.2023.2264452","url":null,"abstract":"<div><div>In this study, a new deep eutectic mixture (DEM) was prepared from <em>D</em>-fructose, <em>L</em>-arginine, and urea and characterized by Fourier transform infrared (FT-IR), refractive index measurement, and thermogravimetric analysis (TGA). In continue this mixture was used as a green catalyst to promote the synthesis of three important derivatives of heterocyclic compounds. The highlights of this work include some notable advantages such as ease of the preparation and simple catalytic process, low cost, green reaction conditions, biodegradability of the catalyst, short reaction times, high yields of the products and simple work-up. Also, the catalyst could be recovered easily and reused up to several times without significant loss of catalytic activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135093988","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2264454
The DMSO/I2 mediated cyclization reaction of (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one afforded the 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one (DMPC). DMPC was characterized by FT-IR, 1H NMR, 13C NMR and HRMS techniques. DMPC was screened for their in vitro antibacterial activity against four bacterial strains namely E. coli, B. subtilis, S. aureus, and Streptococcus spp. and antifungal activity against R. oryzae, P. chrysogenum, A. niger, and C. albicans fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal properties. DMPC possesed potent antibacterial activity against Streptococcus spp. while the powerful antifungal action was found against P. chrysogenum. Besides % free radical scavenging activity was accessed using DPPH and OH assays. DMPC was found to be more active DPPH radical scavenger than OH radical. Theoretical investigation of DMPC was carried out by density functional theory (DFT) method at the B3LYP/6-311++G(d,p) level of theory. Computational investigation of molecular structure, MESP, and HOMO–LUMO was performed to study DMPC. The calculated energy gap of FMOs was found to be 4.25 eV for DMPC. In the MESP plot, the most electronegative potential region found around the oxygen atom. The theoretical and experimental NMR was correlated and correct NMR assignments have been made. Based on the physicochemical features, lipophilicity, water solubility, pharmacokinetic characteristics, and drug similarity matching investigations, the DMPC was revealed to have favorable biological qualities.
{"title":"Synthesis, Computational, Antimicrobial, Antioxidant, and ADME Study of 2-(3,4-Dimethoxyphenyl)-4H-Chromen-4-One","authors":"","doi":"10.1080/10406638.2023.2264454","DOIUrl":"10.1080/10406638.2023.2264454","url":null,"abstract":"<div><div>The DMSO/I<sub>2</sub> mediated cyclization reaction of (<em>E</em>)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one afforded the 2-(3,4-dimethoxyphenyl)-4<em>H</em>-chromen-4-one (DMPC). DMPC was characterized by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS techniques. DMPC was screened for their <em>in vitro</em> antibacterial activity against four bacterial strains namely <em>E. coli</em>, <em>B. subtilis</em>, <em>S. aureus</em>, and <em>Streptococcus spp</em>. and antifungal activity against <em>R. oryzae</em>, <em>P. chrysogenum</em>, <em>A. niger</em>, and <em>C. albicans</em> fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal properties. DMPC possesed potent antibacterial activity against <em>Streptococcus spp</em>. while the powerful antifungal action was found against <em>P. chrysogenum.</em> Besides % free radical scavenging activity was accessed using DPPH and OH assays. DMPC was found to be more active DPPH radical scavenger than OH radical. Theoretical investigation of DMPC was carried out by density functional theory (DFT) method at the B3LYP/6-311++G(d,p) level of theory. Computational investigation of molecular structure, MESP, and HOMO–LUMO was performed to study DMPC. The calculated energy gap of FMOs was found to be 4.25 eV for DMPC. In the MESP plot, the most electronegative potential region found around the oxygen atom. The theoretical and experimental NMR was correlated and correct NMR assignments have been made. Based on the physicochemical features, lipophilicity, water solubility, pharmacokinetic characteristics, and drug similarity matching investigations, the DMPC was revealed to have favorable biological qualities.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135094572","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2261586
The p-methoxycinnamoyl group contained in the compounds extracted from Scrophularia buergeriana, which is a traditional medicinal herb in China, exhibits a remarkable neuroprotective effect. Based on the p-methoxycinnamoyl group, these two cinnamide derivatives, namely, (E)-3-(4-bromophenyl)-1-(4-(4-chlorobenzyl)piperazin-1-yl)prop-2-en-1-one (6a) and (E)-1-(4-(4-chlorobenzyl)piperazin-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one (6b), were designed and synthesized. The target compounds were represented by High-resolution mass spectra, 1H NMR spectra, 13C NMR spectra, and single-crystal X-ray diffraction. According to the results of single-crystal X-ray diffraction, indicating that compound 6a crystallizes in the monoclinic system and compound 6b crystallizes in the triclinic system, and they both have a stacked-layer 3-D structure. Hirshfeld surface indicated that compounds 6a and 6b exist H…H, O…H, C…H, and π…π intermolecular interactions. Furthermore, their neuroprotective effects were further evaluated against glutamate-induced PC12 cell injury. These results indicate that the target compounds exhibit potent activities against glutamine-induced neurotoxicity in PC12 cells. In vivo experiments demonstrated that compounds 6a and 6b have good protective effects in high doses on bilateral common carotid artery ligation.
{"title":"Synthesis, Crystal Structure, Hirshfeld Surface Analyses and Biological Activity of Novel Cinnamide Derivatives as Neuroprotective Drugs","authors":"","doi":"10.1080/10406638.2023.2261586","DOIUrl":"10.1080/10406638.2023.2261586","url":null,"abstract":"<div><div>The <em>p</em>-methoxycinnamoyl group contained in the compounds extracted from <em>Scrophularia buergeriana</em>, which is a traditional medicinal herb in China, exhibits a remarkable neuroprotective effect. Based on the <em>p</em>-methoxycinnamoyl group, these two cinnamide derivatives, namely, (<em>E</em>)-3-(4-bromophenyl)-1-(4-(4-chlorobenzyl)piperazin-1-yl)prop-2-en-1-one (<strong>6a</strong>) and (<em>E</em>)-1-(4-(4-chlorobenzyl)piperazin-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one (<strong>6b</strong>), were designed and synthesized. The target compounds were represented by High-resolution mass spectra, <sup>1</sup>H NMR spectra, <sup>13</sup>C NMR spectra, and single-crystal X-ray diffraction. According to the results of single-crystal X-ray diffraction, indicating that compound <strong>6a</strong> crystallizes in the monoclinic system and compound <strong>6b</strong> crystallizes in the triclinic system, and they both have a stacked-layer 3-D structure. Hirshfeld surface indicated that compounds <strong>6a</strong> and <strong>6b</strong> exist H…H, O…H, C…H, and π…π intermolecular interactions. Furthermore, their neuroprotective effects were further evaluated against glutamate-induced PC12 cell injury. These results indicate that the target compounds exhibit potent activities against glutamine-induced neurotoxicity in PC12 cells. <em>In vivo</em> experiments demonstrated that compounds <strong>6a</strong> and <strong>6b</strong> have good protective effects in high doses on bilateral common carotid artery ligation.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135245929","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2261595
New hybrid compounds were successfully prepared from highly substituted imidazoles and 1,2,3-triazoles using copper-catalyzed click reactions. Also, an efficient method described for the synthesis of tri- and tetrasubstituted imidazoles in the presence of ZnCl2/urea as an efficient catalyst by multi-component reaction under solvent-free conditions. The advantages of this one-pot methodology are experimental simplicity, easy work-up, and afford desired products with high to excellent yields.
{"title":"New Hybrid Compounds from Imidazole and 1,2,3-Triazole: efficient Synthesis of Highly Substituted Imidazoles and Construction of Their Novel Hybrid Compounds by Copper-Catalyzed Click Reaction","authors":"","doi":"10.1080/10406638.2023.2261595","DOIUrl":"10.1080/10406638.2023.2261595","url":null,"abstract":"<div><div>New hybrid compounds were successfully prepared from highly substituted imidazoles and 1,2,3-triazoles using copper-catalyzed click reactions. Also, an efficient method described for the synthesis of tri- and tetrasubstituted imidazoles in the presence of ZnCl<sub>2</sub>/urea as an efficient catalyst by multi-component reaction under solvent-free conditions. The advantages of this one-pot methodology are experimental simplicity, easy work-up, and afford desired products with high to excellent yields.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135536487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2266094
In this study, the antifungal compound 3,5-Diamino-1,2,4-Triazolinium picrate (3,5-DTAZPA) crystals were fully grown and characterized using FT-Raman and FT-IR experiment techniques. Computational methods of 3,5-DTAZPA were performed up to B3LYP with a 6–311++G (d, p) basis set. The Optimized geometry and natural bond orbital (NBO) analysis were been carried out with the help of density functional theory (DFT). The vibrational assignments related to different modes of vibrations were built up by normal coordinate analysis (NCA). Frontier molecular orbital theory (HOMO-LUMO), molecular electrostatic potential (MEP) and Fukui functions were computed. reduced density gradient (RDG), the electron density’s topology and hydrogen bonds were analyzed. The Kirby–Bauer method was employed to assess 3,5-DTAZPA compound’s in vitro antifungal properties against fungal strains. The docking calculations were also carried out with the target protein.
{"title":"Synthesis, Antifungal Activity, Molecular Docking Studies, RDG Analysis, and DFT Computations on Structural Vibrational and Electronic Spectra of 3,5-Diamino-1,2,4-Triazolinium Picrate","authors":"","doi":"10.1080/10406638.2023.2266094","DOIUrl":"10.1080/10406638.2023.2266094","url":null,"abstract":"<div><div>In this study, the antifungal compound 3,5-Diamino-1,2,4-Triazolinium picrate (3,5-DTAZPA) crystals were fully grown and characterized using FT-Raman and FT-IR experiment techniques. Computational methods of 3,5-DTAZPA were performed up to B3LYP with a 6–311++G (d, p) basis set. The Optimized geometry and natural bond orbital (NBO) analysis were been carried out with the help of density functional theory (DFT). The vibrational assignments related to different modes of vibrations were built up by normal coordinate analysis (NCA). Frontier molecular orbital theory (HOMO-LUMO), molecular electrostatic potential (MEP) and Fukui functions were computed. reduced density gradient (RDG), the electron density’s topology and hydrogen bonds were analyzed. The Kirby–Bauer method was employed to assess 3,5-DTAZPA compound’s <em>in vitro</em> antifungal properties against fungal strains. The docking calculations were also carried out with the target protein.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135729155","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2266090
For the first time, Gd2ZnMnO6/ZnO ceramic nanocomposites (Gd2ZnMnO6/ZnO CNCs) were fabricated by a sol-gel auto-combustion process on the basis of a reaction between Gd, Zn and Mn nitrates and saffron as a green fuel. Gd2ZnMnO6/ZnO ceramic nanocomposites were greenly formed using saffron as a novel fuel and stabilizing agent. The morphology, phase, and anatomical purity of Gd2ZnMnO6/ZnO ceramic nanocomposites could be arranged by quantity and type of fuel, temperature, and reaction period. The specimens were explored by various microscopic and spectroscopic approaches. The uncontrolled release of carbon dioxide (CO2) by industrial processes that acidify the oceans and warm the planet has prompted scientists to try different methods to capture CO2 directly from waste water sources. The fabrication of green nanocatalysts with chemical modifications to create value-added products has many benefits. Considering the morphology of Gd2ZnMnO6/ZnO, an appropriate exteriorlayer for CO2 imbibition was created in all catalystsites. Findings disclosed that Gd2ZnMnO6/ZnO positively affected the fabrication yield of 3-aryl-2-oxazolidinones by carbon dioxide, olefins, and anilines. The product was obtained with an excellent yield of 98%. This high yield was obtained in very mild conditions, such as a pressure of 2.5 atm of carbon dioxide at 80 °C for 3 h. The technique enjoyed profitable performance and forbearance of functional groups. The retrievable catalyst was recycled up to ten times for synthesis of 3-aryl-2-oxazolidinones without significant loss in its activity.
{"title":"Gd2ZnMnO6/ZnO Ceramic Nanocomposites for the Cycloaddition of Carbon Dioxide, Amines, and Alkenes under Mild Conditions","authors":"","doi":"10.1080/10406638.2023.2266090","DOIUrl":"10.1080/10406638.2023.2266090","url":null,"abstract":"<div><div>For the first time, Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO ceramic nanocomposites (Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO CNCs) were fabricated by a sol-gel auto-combustion process on the basis of a reaction between Gd, Zn and Mn nitrates and saffron as a green fuel. Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO ceramic nanocomposites were greenly formed using saffron as a novel fuel and stabilizing agent. The morphology, phase, and anatomical purity of Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO ceramic nanocomposites could be arranged by quantity and type of fuel, temperature, and reaction period. The specimens were explored by various microscopic and spectroscopic approaches. The uncontrolled release of carbon dioxide (CO<sub>2</sub>) by industrial processes that acidify the oceans and warm the planet has prompted scientists to try different methods to capture CO<sub>2</sub> directly from waste water sources. The fabrication of green nanocatalysts with chemical modifications to create value-added products has many benefits. Considering the morphology of Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO, an appropriate exteriorlayer for CO<sub>2</sub> imbibition was created in all catalystsites. Findings disclosed that Gd<sub>2</sub>ZnMnO<sub>6</sub>/ZnO positively affected the fabrication yield of 3-aryl-2-oxazolidinones by carbon dioxide, olefins, and anilines. The product was obtained with an excellent yield of 98%. This high yield was obtained in very mild conditions, such as a pressure of 2.5 atm of carbon dioxide at 80 °C for 3 h. The technique enjoyed profitable performance and forbearance of functional groups. The retrievable catalyst was recycled up to ten times for synthesis of 3-aryl-2-oxazolidinones without significant loss in its activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135887919","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2262697
Degree-based topological indices are very useful tools to model and characterize the molecular structure of drugs in order to predict their physicochemical properties without going into laborious and time-consuming laboratory experiments. These indices are numerical descriptors derived for the molecular structures using the principles of graph theory. Degree-based topological indices play a vital role in the QSPR analysis of heart attack drugs by providing molecular descriptors to predict their properties. The main goal of this paper is to compute six degree-based topological indices and a regression model for seven heart attack drugs. These drugs are nitroglycerin, clopidogrel, beta-blockers (metoprolol), ACE inhibitors (lisinopril), statins (atorvastatin), (ARBs) losartan, and beta-adrenergic blockers (propranolol). Regression analysis and degree-based indices correlate with various physicochemical properties related to drug activities, such as molecular weight, complexity, melting point, and boiling point. Correlations provide insights into how the molecular structure influences these properties, helping design and optimize new drugs. In the results, various statistical parameters are used to analyze heart attack drugs.
{"title":"QSPR Analysis of Some Important Drugs Used in Heart Attack Treatment via Degree-Based Topological Indices and Regression Models","authors":"","doi":"10.1080/10406638.2023.2262697","DOIUrl":"10.1080/10406638.2023.2262697","url":null,"abstract":"<div><div>Degree-based topological indices are very useful tools to model and characterize the molecular structure of drugs in order to predict their physicochemical properties without going into laborious and time-consuming laboratory experiments. These indices are numerical descriptors derived for the molecular structures using the principles of graph theory. Degree-based topological indices play a vital role in the QSPR analysis of heart attack drugs by providing molecular descriptors to predict their properties. The main goal of this paper is to compute six degree-based topological indices and a regression model for seven heart attack drugs. These drugs are nitroglycerin, clopidogrel, beta-blockers (metoprolol), ACE inhibitors (lisinopril), statins (atorvastatin), (ARBs) losartan, and beta-adrenergic blockers (propranolol). Regression analysis and degree-based indices correlate with various physicochemical properties related to drug activities, such as molecular weight, complexity, melting point, and boiling point. Correlations provide insights into how the molecular structure influences these properties, helping design and optimize new drugs. In the results, various statistical parameters are used to analyze heart attack drugs.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136014085","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2259572
Under solvent-free conditions and with the help of ultrasonic irradiation, the synthesis of pyrano[3,2-c]chromen and pyrano[3,2-c]quinolin derivatives was promoted by four different ionic liquids. All reaction was performed at 100 °C and had good to excellent yields. 1-butyl-1-methylpyrrolidin-1-ium acetate (A), 1-butyl-1-methylpiperidin-1-ium acetate (B), N,N,N-triethylbutan-1-aminium acetate (C), and tetrabutylammonium acetate (D) as perfect ionic liquids for this reaction show remarkable catalytic activity. The work was simply developed for the reaction of chalcones with 4-hydroxy-1-methylquinolin-2(1H)-one/4-hydroxycoumarin to perform pure products of pyran heterocycles.
{"title":"Acidic Ionic Liquids in Ultrasonic Irradiation Conditions Promote the Nucleophilic Addition to Chalcone Derivatives","authors":"","doi":"10.1080/10406638.2023.2259572","DOIUrl":"10.1080/10406638.2023.2259572","url":null,"abstract":"<div><div>Under solvent-free conditions and with the help of ultrasonic irradiation, the synthesis of pyrano[3,2-c]chromen and pyrano[3,2-c]quinolin derivatives was promoted by four different ionic liquids. All reaction was performed at 100 °C and had good to excellent yields. 1-butyl-1-methylpyrrolidin-1-ium acetate <strong>(A)</strong>, 1-butyl-1-methylpiperidin-1-ium acetate <strong>(B)</strong>, <em>N,N,N</em>-triethylbutan-1-aminium acetate <strong>(C)</strong>, and tetrabutylammonium acetate <strong>(D)</strong> as perfect ionic liquids for this reaction show remarkable catalytic activity. The work was simply developed for the reaction of chalcones with 4-hydroxy-1-methylquinolin-2(1H)-one/4-hydroxycoumarin to perform pure products of pyran heterocycles.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136135860","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2265025
A novel catalyst of cesium-loaded boron nitride (Cs-BNT) was synthesized by stirring the materials at room temperature and was subsequently characterized by the spectroscopic techniques SEM, SEM-EDX, SEM-Mapping, TEM, Brunauer–Emmett–Teller (BET), DSC-TGA, Fourier transform infrared spectroscopy (FT-IR), and Raman spectrum. Furthermore, the catalyst of CsBN layer theoretically analyzed. The microwave method by Cs-BNT was used to synthesize novel heterocyclic quinoline-bearing dihydropyridines 5a-l and subsequently characterized using FT-IR, 1H NMR, 13C NMR, and mass spectrometry. An efficient, recyclable property of the catalyst was recognized, and it was observed that it could show more than five times efficiency in reusability without significant loss of its catalytic activity. The compound diethyl-6-amino-5-cyano-1-(4-fluorophenyl)-4-(2-methoxyquinolin-3-yl)-1,4-dihydropyridine-2,3-dicarboxylate hit compound revealed EHOMO-ELUMO as 4.00 eV indicating high stability of the molecule. The band structure, geometry, DOS, PDOS and Mulliken population based on DFT studies complemented the experimental results.
{"title":"Microwave Hantzsch Synthesis of Quinolinyl-Dihydropyridines Supported by Cs-BNT Catalyst and DFT Investigations","authors":"","doi":"10.1080/10406638.2023.2265025","DOIUrl":"10.1080/10406638.2023.2265025","url":null,"abstract":"<div><div>A novel catalyst of cesium-loaded boron nitride (Cs-BNT) was synthesized by stirring the materials at room temperature and was subsequently characterized by the spectroscopic techniques SEM, SEM-EDX, SEM-Mapping, TEM, Brunauer–Emmett–Teller (BET), DSC-TGA, Fourier transform infrared spectroscopy (FT-IR), and Raman spectrum. Furthermore, the catalyst of CsBN layer theoretically analyzed. The microwave method by Cs-BNT was used to synthesize novel heterocyclic quinoline-bearing dihydropyridines <strong>5a-l</strong> and subsequently characterized using FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass spectrometry. An efficient, recyclable property of the catalyst was recognized, and it was observed that it could show more than five times efficiency in reusability without significant loss of its catalytic activity. The compound diethyl-6-amino-5-cyano-1-(4-fluorophenyl)-4-(2-methoxyquinolin-3-yl)-1,4-dihydropyridine-2,3-dicarboxylate hit compound revealed E<sub>HOMO-</sub>E<sub>LUMO</sub> as 4.00 eV indicating high stability of the molecule. The band structure, geometry, DOS, PDOS and Mulliken population based on DFT studies complemented the experimental results.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135096549","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2261591
This study includes the evaluation of most stable structure, frontier molecular orbitals, molecular electrostatic potential (MEP), and nonlinear optical (NLO) parameters of 2,4-dimethylaniline (2,4DMA), 2,5-dimethylaniline (2,5DMA), and 2,6-dimethylaniline (2,6DMA) using density functional theory (DFT) employing B3LYP functional with 6-311++G(d,p) basis set. HOMO-LUMO energies, band gap energies, and global reactivity descriptors were obtained from the optimized structures. The band gap energy was determined as 3.7865, 3.9348, and 3.9443 eV for 2,4DMA, 25DMA, and 2,6DMA, respectively. The reactive sites of the molecules were obtained from the molecular electrostatic potential energy. The NLO parameters such as dipole moment, polarizability, and hyperpolarizability have been investigated for the title molecules. The investigated dipole moment and first-order hyperpolarizability values are higher than the prototypical value of urea and show good NLO behavior. The NMR chemical shifts, electronic absorption spectra, and charge distribution of atoms were calculated theoretically. Furthermore, thermodynamic and rotational constants were also calculated.
{"title":"Structure, Frontier Molecular Orbitals, MEP, Charge Analysis, and NLO Study of 2,4-, 2,5-, and 2,6-Dimethylanilines Using DFT","authors":"","doi":"10.1080/10406638.2023.2261591","DOIUrl":"10.1080/10406638.2023.2261591","url":null,"abstract":"<div><div>This study includes the evaluation of most stable structure, frontier molecular orbitals, molecular electrostatic potential (MEP), and nonlinear optical (NLO) parameters of 2,4-dimethylaniline (2,4DMA), 2,5-dimethylaniline (2,5DMA), and 2,6-dimethylaniline (2,6DMA) using density functional theory (DFT) employing B3LYP functional with 6-311++G(d,p) basis set. HOMO-LUMO energies, band gap energies, and global reactivity descriptors were obtained from the optimized structures. The band gap energy was determined as 3.7865, 3.9348, and 3.9443 eV for 2,4DMA, 25DMA, and 2,6DMA, respectively. The reactive sites of the molecules were obtained from the molecular electrostatic potential energy. The NLO parameters such as dipole moment, polarizability, and hyperpolarizability have been investigated for the title molecules. The investigated dipole moment and first-order hyperpolarizability values are higher than the prototypical value of urea and show good NLO behavior. The NMR chemical shifts, electronic absorption spectra, and charge distribution of atoms were calculated theoretically. Furthermore, thermodynamic and rotational constants were also calculated.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135536334","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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