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Cooperative Regulation of s Lone-Pair Expression Realizes Distinct Excitonic Emissions in Hybrid Germanium, Tin, and Lead Halides.
J Am Chem Soc
December 2024
Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, Guangdong 518055, China.
Lone-pair expression is significantly influenced by geometric constraints in hybrid metal halides (HMHs). Two-dimensional (2D) HMHs possess reduced structural dimensionality, allowing for a wide range of off-center displacement of the metal center. However, the effect of lone-pair-induced off-center distortion on the geometric configuration of inorganic units, electronic properties, and exciton emissions in 2D HMHs remains unclear.
View Article and Find Full Text PDFFluorination Affects the Force Sensitivity and Nonequilibrium Dynamics of the Mechanochemical Unzipping of Ladderanes.
J Am Chem Soc
November 2024
Department of Chemistry, Stanford University, Stanford, California 94305, United States.
When multiple reaction steps occur before thermal equilibration, kinetic energy from one reaction step can influence overall product distributions in ways that are not well predicted by transition state theory. An understanding of how the structural features of mechanophores, such as substitutions, affect reactivity, product distribution, and the extent of dynamic effects in the mechanochemical manifolds is necessary for designing chemical reactions and responsive materials. We synthesized two tetrafluorinated [4]-ladderanes with fluorination on different rungs and found that the fluorination pattern influenced the force sensitivity and stereochemical distribution of products in the mechanochemistry of these fluorinated ladderanes.
View Article and Find Full Text PDFEscape from Flatland: Stereoselective Synthesis of Hexa-aryl Borazines and their sp²-Based 3D Architectures.
Angew Chem Int Ed Engl
November 2024
University of Vienna Faculty of Chemistry: Universitat Wien Fakultat fur Chemie, Institute of Organic Chemistry, Währinger Strasse 38, 1090, Vienna, AUSTRIA.
Borazine and its derivatives can be considered critical doping units for engineering hybrid C(sp2)-based molecules with tailored optoelectronic properties. Herein, we report the first synthesis of hexaarylborazines that, bearing ortho-substituted aryl moieties, extend three-dimensionally. Using a one-pot protocol, we first form an electrophilic chloroborazole and then react it with an aryl lithium (ArLi).
View Article and Find Full Text PDF2-Halomethyleneoxetanes from 2-Methyleneoxetanes by Reaction with -Halosuccinimides: Reactant Influences on Stereochemical Outcomes and Reaction Pathways.
J Org Chem
November 2024
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
The first general synthesis of 2-halomethyleneoxetanes, realized by the reaction of 2-methyleneoxetanes with -halosuccinimides (NXS), is reported. The relative diastereoselectivities of the transformations were dependent on the halogen of NXS, while alternative reaction outcomes were influenced by substituents on the oxetane. Quantum mechanical calculations and molecular dynamics simulations exploring the basis of the observed diastereoselectivities are described.
View Article and Find Full Text PDFLigand-Enabled Cu-Catalyzed Stereoselective Synthesis of P-Stereogenic ProTides.
J Am Chem Soc
November 2024
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, China.
Nucleoside analogues have seen significant advancements in treating viral infections and cancer through ProTide technology, leading to a series of FDA-approved drugs such as sofosbuvir, tenofovir alafenamide, and remdesivir. The stereochemical configuration at the phosphorus center of ProTides significantly influences their pharmacological properties, necessitating efficient stereoselective synthesis. Traditional methods using chiral auxiliaries or nonracemic phosphorylating agents are labor-intensive and inefficient, while recent organocatalytic approaches, despite their promise, still face limitations.
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