Understanding the Regioselectivity and the Molecular Mechanism of [3+2] Cycloaddition Reactions between Nitrous Oxide and Conjugated Nitroalkenes: A DFT Computational Study

Article Chemistry, Organic

Stepwise, zwitterionic course of hetero-Diels-Alder reaction between 1,2,4-triazine molecular systems and 2-cyclopropylidene-1,3-dimethylimidazoline

Radomir Jasinski

Summary: The computational study provides clear evidence for the polar, stepwise mechanism of hetero-Diels-Alder reactions, using the specific example of 5,6-diphenyl-1,2,4-triazine and 2-cyclopropylidene-1,3-dimethylimidazoline.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2022)

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Review Chemistry, Medicinal

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

Saul Noriega et al.

Summary: The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. The nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules and exhibits a wide spectrum of activities, including antimicrobial activity. The properties of nitro compounds have a deep effect on the resulting molecules' polarity, electronic properties, and interactions with amino acids in proteins.

PHARMACEUTICALS (2022)

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Article Chemistry, Physical

Understanding the uniqueness of the stepwise [4+1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Agnieszka Kacka-Zych

Summary: The [4 + 1] cycloaddition and [2 + 1] cycloaddition reactions of alpha-halogeno-nitroalkenes with carbene were studied using density functional theory calculations. The reactions proceed through different mechanisms and pathways, indicating distinct reaction behaviors.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2021)

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Article Chemistry, Organic

Synthesis and anticancer activity of 11-azaartemisinin derivatives bearing 1,2,3-triazole moiety

Dung Tien Nguyen et al.

Summary: The synthesized artemisinin derivatives showed good cytotoxic activity against KB and HepG2 cell lines, with IC50 values ranging from 4.27 to 70.40 μm. One derivative exhibited the highest activity with IC50 values of 10.18 and 4.27 μm for KB and HepG2 cell lines, respectively.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2021)

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Article Chemistry, Organic

Synthesis and biological evaluation of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones as topoisomerase I inhibitors

Laichun Luo et al.

Summary: A series of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones were designed, synthesized, and evaluated as anticancer agents. Among them, two compounds demonstrated potent cytotoxicity and topoisomerase I inhibitory activity, and their possible binding modes with topoisomerase I/DNA complex were proposed based on molecular docking results.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2021)

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Article Green & Sustainable Science & Technology

Green synthesis of nitrocyclopropane-type precursors of inhibitors for the maturation of fruits and vegetables via domino reactions of diazoalkanes with 2-nitroprop-1-ene

Agnieszka Fryzlewicz et al.

Summary: The article introduces a green and selective methodology for preparing precursors of cyclopropene-type inhibitors for fruit or vegetable maturation, and explores the reaction mechanism in detail through advanced quantum chemical calculations. The synthesized compounds were fully characterized using spectral methods and structural X-ray diffraction, enabling the programming of a wide range of similar compound synthesis.

JOURNAL OF CLEANER PRODUCTION (2021)

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Article Chemistry, Physical

Perfluorobicyclo[2.2.0]hex-1(4)-ene as unique partner for Diels-Alder reactions with benzene: a density functional theory study

Agnieszka Kacka-Zych et al.

Summary: Using density functional theory, the mechanism of Diels-Alder reactions between perfluorobicyclo[2.2.0]hex-1(4)-ene and bicyclo[2.2.0]hex-1(4)-ene with benzene and naphthalene has been studied, revealing the bonding pattern and changes in electron density along the reaction paths. Analysis showed that the reactions proceed through a synchronous and non-concerted one-step mechanism with moderate activation energy, and perfluorobicyclo[2.2.0]hex-1(4)-ene exhibits higher reactivity.

THEORETICAL CHEMISTRY ACCOUNTS (2021)

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Article Biochemistry & Molecular Biology

The Participation of 3,3,3-Trichloro-1-nitroprop-1-ene in the [3+2] Cycloaddition Reaction with Selected Nitrile N-Oxides in the Light of the Experimental and MEDT Quantum Chemical Study

Karolina Zawadzinska et al.

Summary: The regioselective [3 + 2] cycloaddition reactions of aryl-substituted nitrile N-oxides with trichloronitropropene were studied experimentally and theoretically. The reactions have moderate activation Gibbs free energies and are irreversible and kinetically controlled. The differences in reactivity were found to be due to the nucleophilic activation and polar character of the reactions.

MOLECULES (2021)

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Article Chemistry, Multidisciplinary

Understanding the molecular mechanism of γ-elimination of nitrous acid in the framework of the molecular electron density theory

Agnieszka Kacka-Zych et al.

Summary: The gamma-dehydronitration reactions of furaxanenitrolic acids were studied using density functional theory, revealing changes in bonding and electron density characteristics that indicate a non-concerted nature of the molecular mechanism.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Analysis of the possibility and molecular mechanism of carbon dioxide consumption in the Diets-Alder processes

Karolina Kula et al.

Summary: The significant increase in carbon dioxide concentration in the Earth's atmosphere is a serious issue for humanity, and current trends in modern chemistry and chemical technology involve its utilization. Research is being done on the consumption of CO2 through Diels-Alder processes under different conditions to synthesize a wide range of internal carboxylates.

PURE AND APPLIED CHEMISTRY (2021)

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Review Chemistry, Organic

Multicomponent Reactions Based on In Situ Generated Isocyanides for the Construction of Heterocycles

Subrahmanya Ishwar Bhat et al.

Summary: Isocyanides, with a long history and high versatility, have been widely used in multicomponent synthesis, but their strong fetid odor, lability, and potential toxicity have made researchers worldwide hesitant to use them. In situ generation and capturing synthetic protocols may offer a sustainable alternative to conventional use, making it the main focus of this review. Analysis of literature reports from 2005-2020 and discussion on reaction conditions and mechanisms aim to provide readers with a better understanding of in situ versions and insights for further investigations.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2021)

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Article Biochemistry & Molecular Biology

The Molecular Mechanism of the Formation of Four-Membered Cyclic Nitronates and Their Retro (3+2) Cycloaddition: A DFT Mechanistic Study

Agnieszka Kacka-Zych

Summary: The formation of cyclic nitronates and the retro-32CA reaction of 4H-[1,2]oxazete 2-oxide were studied using density functional theory method. The formation of 4,4-di-tert-butyl-3-nitromethyl-4H-[1,2]oxazete 2-oxide proceeds through a one-step mechanism, while the retro-32CA leading to ketone and nitrile oxide derivative is described as an asynchronous two-stage one-step process.

MOLECULES (2021)

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Article Chemistry, Organic