Letters in Organic Chemistry - Online First
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21 - 25 of 25 results
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Rotational Barrier and Origin of Substituent Effect on Bond Dissociation Enthalpy of Para-substituted Anilines, Benzaldehydes, and Toluenes
Authors: Ali H. Yateem and Abdulrahman AllangawiAvailable online: 29 May 2025More LessUnderstanding the rotational barriers (RBs) and bond dissociation enthalpies (BDEt) of substituted aromatic compounds is crucial for predicting their chemical reactivity and stability. The RBs for 26 varying para-substituted anilines, benzaldehydes, and toluenes around the respective phenyl-NH2, -CHO, and -CH3 bonds, as well as around the corresponding radical phenyl-NH, -CO, and -CH2 bonds, were computed, based on the Density Functional Theory (DFT). The BDEt of the aminic N-H, CO-H, and methyl C-H bonds in the respective neutral molecules was also computed. The RBs and various geometric, molecular, and atomic properties were used to explain how the substituents influence the BDEt. The trends were rationalized by considering the relative stabilization/destabilization of the parent neutral molecules versus the corresponding radicals. This study is the first in which trends in the RBs and BDEts are rationalized by considering the effect of substituent, providing valuable information for understanding the fundamental behavior of substituted aromatics.
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Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate Ionic Liquid: An Efficient Catalyst for the Synthesis of 2,4,5-triaryl-1H-imidazole Derivatives
Available online: 21 May 2025More LessHerein, we disclose an eco-friendly route for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives. One-pot, three-component synthesis involving benzil, substituted aromatic aldehydes, and ammonium acetate in the presence of a catalytic amount of trihexyltetradecyl-phosphonium bis(2,4,4-trimethylpentyl)phosphinate (PBIL) ionic liquid in ethanol at room temperature yields corresponding 2,4,5-triaryl-1H-imidazole derivatives in appreciable yield. The use of ionic liquid as a green catalyst with ethanol, which is considered to be an environmentally benign solvent, simple workup procedure, and appreciable yield of the product are some of the notable advantages of this method.
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Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies
Available online: 09 May 2025More LessThe current work describes a unique iodine-mediated intra-molecular rearrangement of amide to nitrile and thiourea to urea, which took place simultaneously in thiophenes. The thiophenes having amide and amine groups at the adjacent positions were prepared via the Gewald reaction and subsequently treated with isothiocyanates in the presence of molecular iodine to get 1-(3-cyanothiophen-2-yl)-3-phenylureas in good yields. The synthesized compounds are of particular interest both chemically and biologically, as they contain thiophene, urea, and nitrile moieties in a single molecule. Many thiophene derivatives have been reported to exhibit antioxidant properties. Hence, the synthesized molecules were screened for their antioxidant activity by means of scavenger activity towards 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the Ferric Ion Reducing Power (FRAP) assay. Some compounds exhibited promising antioxidant properties.
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A Unique and Innovative Rainwater-assisted Synthesis of Quinoxalines
Authors: Shikha Sharma and Bimal Krishna BanikAvailable online: 30 April 2025More LessA novel and efficient method for synthesizing various quinoxaline derivatives has been developed, utilizing rainwater as both a solvent and a catalyst. This approach represents a significant advancement in green chemistry, as it combines simplicity, rapidity, and convenience while avoiding the need for toxic or expensive reagents. The synthesis involves the condensation reaction of aromatic 1,2-diamines with aromatic 1,2-dicarbonyl compounds. Traditionally, these reactions require specialized solvents and catalysts, but in this method, rainwater serves a dual function, streamlining the process and minimizing environmental impact. The use of rainwater not only simplifies the reaction setup but also provides an eco-friendly alternative to conventional organic solvents. The condensation leads to the formation of quinoxaline derivatives, a class of compounds known for their diverse biological and pharmacological activities. The reaction proceeds smoothly at ambient temperature, significantly reducing the energy requirements typically associated with chemical syntheses. This innovative synthesis method demonstrates the potential of using natural resources like rainwater in chemical reactions, contributing to sustainable practices in the field of organic synthesis. The versatility of the approach allows for the preparation of a variety of quinoxalines, offering promising applications in medicinal chemistry and material science. The rapid and straightforward process opens new avenues for the synthesis of quinoxalines, showcasing the potential of rainwater as a green solvent and catalyst in synthetic chemistry.
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Synthesis of 3, 3-Di(indolyl)indolin-2-one in the Presence of Iron Nanocatalysts
Authors: Seyyedeh Masoumeh Zakariaie and Bita BaghernejadAvailable online: 27 March 2025More Less3, 3-di(indolyl)indolin-2-one derivatives have attracted the attention of researchers due to their various biological and medicinal applications. Due to the significant importance of indole compounds, various methods with different conditions and catalysts have been used for their synthesis. However, some of these reactions have disadvantages, such as low efficiency, long reaction time, use of toxic solvents, etc. In the study, iron nanocatalysts have been used as a suitable catalyst to prepare 3, 3-di(indolyl)indolin-2-one derivatives. This method has many advantages compared to other methods and it completes the reaction in a shorter time and with a higher yield, as described in this article.
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