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International Journal of Organic Chemistry
Number of Followers: 10

This is an Open Access Journal

Open Access journal
ISSN (Print) 2161-4687 - ISSN (Online) 2161-4695
Published by Scientific Research Publishing

[243 journals]

Synthesis, Spectrometric Characterization (ESI-MS, NMR, IRTF), X-Ray Study
and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Benzoate
- Abstract: Publication year: 2020Source: American Journal of Organic Chemistry, Volume 10, Number 1Akoun Abou, Abdoulaye Djandé, Amadou Tidjani Ilagouma, Olivier Ouari, Adama SabaThe paper presents a combined experimental and computational study of 7-substituted coumarin derivative, the 2-oxo-2H-chromen-7-yl benzoate (I). The compound was prepared in the laboratory by linking the coumarin system (7-hydroxycoumarin) to benzoyl chloride and crystallized in the monoclinic space group P21 with ð‘Ž = 3.86010(10), ð‘ = 27.7876(9), ð‘ = 5.7453(2) Å, ð›¼ = ð›¾ = 90, ð›½ =91.063(3)° and ð‘ = 2. The compound has been characterized structurally by spectroscopy and by single-crystal X-Ray diffraction. In the latter, the structure of (I) was solved by direct methods and refined to a final R value of 0.038 for 2260 independent reflections. Its structure is stabilized by intramolecular C-H···O and intermolecular C-H···O hydrogen bonds that extended as infinite 1D chain along [001]. Stabilization is also ensured by oxygen-π stacking interaction between the aromatic ring and oxygen of the benzoate moiety. The analysis of intermolecular interactions through the mapping of dnorm and shape-index revel that the most significant contributions to the Hirshfeld surface 36.2 and 27.9% are from H···H and O···H contacts, respectively. Besides, the molecular geometry of (I) was also optimized using density functional theory (DFT/RB3LYP), the basic abinitiomodel i.e the restricted Hartree-Fock (RHF) methods with the 6-311++G(d, p) basis set in ground state and frequency calculations with RB3LYP method using 6-31G(d,p) basis set. The theoretical data resulting from these quantum chemical calculations are generally in good agreement with the observed structure. The only significant observed difference is in the torsion angles between the coumarin ring system and the benzoate ring, where the observed C—O—C—C value (59.6 (4)°) is slightly lower than the DFT/RB3LYP calculated value (54.32°) and the frequency calculations (41.23°) value and larger than that of the RHF computed value (110.63°). The non-linear optical effects (NLO), molecular electrostatic potential (MEP), frontier molecular orbitals (FMO), and the Mulliken charge distribution were also investigated theoretically. The theoretical HOMO–LUMO energy gap values originating from these calculations are 4.465 eV (DFT/RB3LYP/6–311++G(d,p)) and 4.434 eV (FREQ/ RB3LYP/6–31G(d,p)).
Comparison of Various Feedstocks for the Microwave-Assisted Synthesis of
Biodiesel
- Abstract: Publication year: 2019Source: American Journal of Organic Chemistry, Volume 9, Number 2C. Villot, M. E. Howard, K. W. KittredgeThe microwave-assisted acid catalyzed synthesis of biodiesel from various feedstocks are reported. The feedstocks consist of vegetable, canola, olive, avocado, corn, cottonseed and soybean oils and also were compared to a commercial biodiesel sample that was prepared from a mixture of varying oils by GC-MS. All oils gave biodiesel in excellent yields (
Experimental and Computational Study of Antioxidant Activities of
Synthetic Heterocyclic Quinazoline-4-one Derivatives
- Abstract: Publication year: 2019Source: American Journal of Organic Chemistry, Volume 9, Number 1Nagwa M. M. Hamada, Alshimaa Abd ElgawadThe objective of this study was to investigate and evaluate both vanillin and quinazolinone ring systems as anti-radical agents. Herein, we discuss the design strategy and report the synthesis of five novel antioxidants as quinazolinone–vanillin derivatives. The structures of the synthesized heterocyclic compounds have been recognized based on their melting point (m.p.), elemental analysis, IR and 1H & 13C NMR and mass spectroscopic data. In this work, we report a combined experimental and theoretical study of the radical scavenging activity of the synthesized heterocyclic compounds to determine their potential as antioxidants. The optimization of all the synthesized compounds using density functional theory (DFT) at the B3LYP/6-311G (d, p) & 631++ level of theory was established. Radical scavenging activity has been explained based on the energy gap (HOMO–LUMO) and ionization potential (IP) values. The calculations carried out are related to the electronic affinity (EA), hardness (η), softness (S), electronegativity (χ), and electrophilicity (ω). The structure activity relationship has been explained by mapping the electrostatic potential surface (MEP). The results of both experimental and theoretical antioxidant activities of the synthesized molecules have shown that the synthesized compounds (2–4) demonstrated simulated results comparable with those of vanillin, they are good antioxidants and could be effective in fighting oxidative attacks. The results revealed also that the synthesized compounds (5 and 6) are more effective antioxidants than common vanillin and they showed excellent scavenging capacity against DPPH and Nitric oxide (NO).
Synthesis, Characterization, Antioxidant and Antimicrobial Activity of
Copper(II) Complex with Schiff Base Derived from
2,2-dihydroxyindane-1,3-dione and Tryptophan
- Abstract: Publication year: 2019Source: American Journal of Organic Chemistry, Volume 9, Number 1Emir Horozić, Jasmin Suljagić, Mersiha SuljkanovićSchiff bases and complexes are today the subject of many studies because of the established biological, inhibitor and catalytic properties. The aim of this paper is to investigate the interaction of Schiff base obtained by reaction of 2,2-dihydroxyindane-1,3-dione (ninhydrin) and the essential amino acid tryptophan with copper(II) ion. Spectral characterization and examination of the potential antimicrobial and antioxidant activity of the synthesized complex were performed. The imine Cu(II) complex is characterized by FTIR and UV/Vis spectroscopy. Stoichiometric M:L ratio was determined by Joe and Yones method. Antioxidant activity was tested by DPPH and FRAP method. Antibacterial and antifungal activity was determined by diffusion technique on reference strains from the ATCC collection. The results showed that the synthesized Schiff base coordinates the Cu(II) ion as a tridentate ligand, in a molar ratio of 1:2 (M:L). The synthesized complex showed significant antioxidant activity. The antimicrobial effect of the Cu(II) complex in the case of S. aureus, E. faecalis, L. monocytogenes, B. subtilis and C. albicans was obtained, with inhibition zones of 11-20 mm.
Synthesis, Reactions and Biological Importance of α, β-Unsaturated
Carbodithioate Esters: A Review
- Abstract: Publication year: 2019Source: American Journal of Organic Chemistry, Volume 9, Number 1Md. Ashraful Alam, Kazuaki Shimada, Yusuke Taneichi, Md. Wahab Khan, Md. Abdur Rashid, Md. Chanmiya SheikhCarbodithioate esters are important functional organosulfur compounds widely used in different fields such as pharmaceuticals, agrochemicals and material sciences. α, β-unsaturated dithioesters, carbodithioates are the type of organosulfur chemical compounds that attract the special interest of organic chemists. α, β-unsaturated dithioester type compounds have various applications in medicinal chemistry and provided numerous potent α, β-unsaturated dithioester derivatives for different therapeutic targets. α, β-unsaturated dithioesters are widely used as solvents, polymers, and biopharmaceutical agents. For the treatment of tuberculosis, leprosy and dermatitis herpetiformis diseases, several drug molecules containing α, β-unsaturated dithioester groups are used. Based on these applications, researchers have engaged in the preparation and study of many types of α, β-unsaturated dithioester derivatives for their medicinal activities e.g. biological, antimalarial, antimicrobial, anti-inflammatory, anticancer, anti-HIV, and anti-inflammatory properties. The present article provides a targeted review of recent synthetic strategies, pertinent reactions and applications of α, β-unsaturated dithioester type compounds to facilitate future research efforts so that the medicinal and industrial applications of this important class of compounds continue to be beneficial to society.
(Coumarin-3-yl)-benzoates as a Series of New Fluorescent Compounds:
Synthesis, Characterization and Fluorescence Properties in the Solid State
- Abstract: Publication year: 2018Source: American Journal of Organic Chemistry, Volume 8, Number 2Sosso Siaka, Jules Yoda, Abdoulaye Djandé, Bruno Coulomb(Coumarin-3-yl)-benzoates, a series of coumarin derivatives were designed, synthesized and characterized as fluorescent compounds. The structural assignments of these compounds were examined based on their corresponding FT-IR, ESI-MS, and 1H- and 13C-NMR spectral data in addition to their crystal structures determined by X-ray diffractometry. The fluorescence spectra, recorded in the solid state, have been investigated. The effects of various substituents R on fluorescence properties were examined. As a result, compound 2c with an electron-donating substituent (R = t-Bu) exhibited the strongest fluorescence intensity whereas compound 2f with an electron-withdrawing group (R = CN) presented the weakest one.
Strategy for the Construction of Lactones via Ene-reaction
- Abstract: Publication year: 2018Source: American Journal of Organic Chemistry, Volume 8, Number 1Bello Y. MakamaAn effective ene-reaction protocol was developed for the preparation of cis-fused bicyclic lactones catalyzed by various Lewis acids at low temperatures.
Monomodal vs Multimodal Microwave Irradiation Applied in the Synthesis of
Fluorochalcones
- Abstract: Publication year: 2018Source: American Journal of Organic Chemistry, Volume 8, Number 1José Eladio Antonio-Arias, Verónica del C. Díaz-Oliva, Nancy Romero-Ceronio, Abraham Gómez-Rivera, Hidemi Aguilar-Mariscal, Luis F. Roa de la Fuente, Carlos E. Lobato-GarcíaThe synthesis of o-, m- and p-fluorine-substituted chalcones at the ring “B” was accomplished by a Claisen-Schmidt condensation between the benzaldehyde and acetophenone. The reaction was performed in solvent-free conditions with microwave activation and good yields (> 75%) were obtained. It is noteworthy that the application of conventional reaction conditions produced very low yields and in some cases, the reaction did not proceed at all. The methodology implemented considerably reduces reaction times.
Investigation of an Amidation Reaction for the Preparation of Some
2-(2-Phenyl-4-Oxoquinazolin-3(4H)-yl)-N-Substituted Acetamides and
N-Substituted
2-(2-(4-Oxo-2-Phenylquinazolin-3(4H)-yl)Acetylhydrazine-1-Carboxamides
- Abstract: Publication year: 2018Source: American Journal of Organic Chemistry, Volume 8, Number 1Omaima M. Aboul Wafa, Hoda M. G. Daabees, Alaa A. El-Tombary, Eman S. Ezz-El DienA previously reported amide bond formation performed by treating ethyl 2-phenyl-4-oxo-3(4H)quinazolineacetate with the appropriate amine in boiling HOAc to synthesize a series of quinazolin-4-one derivatives was investigated. Elucidation of the structure of the synthesized products by IR, 1H NMR and 13C NMR indicated that, unfortunately, no amide bond was formed. The only product produced in all reactions was 4-oxo-2-phenyl-4(3H)-quinazolineacetic acid even when using different amines. Repeating the afore-mentioned reaction, amide formation was attempted for the synthesis of a series of 4-oxoquinazolinecarboxamide derivatives by treating 2-(2-(4-oxo-2-phenylquinazolin-3(4H)-yl)acetyl)hydrazine carboxylate with the appropriate 1° or 2° amine in boiling HOAc. Unfortunately, the reaction did not proceed as designed and recovery of the starting ester was the only product detected. Structure elucidation of the product obtained was also made by IR, 1H NMR and 13C NMR spectroscopy which indicated that no amide bond was formed. Therefore, in the present investigation, N-substituted acetamide derivatives were synthesized, by using known synthetic approaches, from the corresponding acid via treatment with SOCl2 in different solvent systems followed by amidation with the selected amines.
Investigating the Effect of 2,4-Dinitrophenol on Synthetic Membranes: An
Undergraduate Research Experiment
- Abstract: Publication year: 2017Source: American Journal of Organic Chemistry, Volume 7, Number 2Shadi Abu-Baker, Annette Holstein, Makayla Lancaster, Amber Abram, Shahrokh Ghaffari, Philip Garber, Tanya Whitmer, Indra Sahu2,4-Dinitrophenol’s (2,4-DNP) effect on synthetic membrane proteins was investigated to test if it is selective to cancer-mimic synthetic cell membranes, which are more bountiful in phosphatidylserine (PS) lipids compared to normal cells that have much more phosphatidylcholine (PC) lipids. Three undergraduate students prepared the untreated synthetic membranes and incorporated 2,4-DNP into a second set of treated samples. Students analysed the samples via solid-state 31P NMR. The results indicate that 2,4-DNP breaks down 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-L-serine] (POPS) synthetic membranes, but not 1-palmitoyl-2-oleoyl -sn-glycero-3-phosphocholine (POPC) membranes that mimic the normal cell membrane composition. The 31P NMR spectrum of the head groups of the membrane suggests that the 2,4-DNP is disturbing the multilamellar vesicles (MLVs) and forming small micelles only in the POPS synthetic membranes.