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A tale of two topological isomers: Uptuning [Fe(O)(Mecyclam)] for olefin epoxidation.
Proc Natl Acad Sci U S A
March 2024
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455.
TMC- and TMC- the two topological isomers of [Fe(O)(TMC)(CHCN)] (TMC = 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane, or Mecyclam), differ in the orientations of their Fe=O units relative to the four methyl groups of the TMC ligand framework. The Fe=O unit of TMC- points away from the four methyl groups, while that of TMC- is surrounded by the methyl groups, resulting in differences in their oxidative reactivities. TMC- reacts with HAT (hydrogen atom transfer) substrates at 1.
View Article and Find Full Text PDFChiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation.
Chem Commun (Camb)
January 2023
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
The chiral weakly coordinating (3,3'-biphenyl-BINOL)BF anion can be generated by the reaction of the BINOL derivative with Cu(NCMe)BF. Structural analysis suggest the anion is weakly coordinating to Cu. However, its use in cyclopropanation reactions leads to the rearrangement of the anion to create a chiral 3,3'-diphenyl-BINOL ligand that coordinates to copper.
View Article and Find Full Text PDFA Tale of Two Isomers: Enhanced Antiaromaticity/Diradical Character versus Deleterious Ring-Opening of Benzofuran-fused s-Indacenes and Dicyclopenta[b,g]naphthalenes.
Angew Chem Int Ed Engl
October 2021
Department of Chemistry and Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253, USA.
Article Synopsis
- The study investigates the effects of combining benzofurans with s-indacene and dicyclopenta[b,g]naphthalene to influence their antiaromaticity and diradical properties.
- Synthesizing the compounds results in two types: syn-IDBF, which shows high paratropicity, and syn-IIDBF, which displays strong diradical character.
- Comparing these to benzothiophene-fused compounds reveals that the presence of oxygen enhances antiaromatic characteristics and paratropicity, while the diradical character of syn-IIDBF increases due to a rearrangement in its naphthalene structure.
Electronic Structure and Vibrational Signatures of the Delocalized Radical in Hydrated Clusters of Copper("II") Hydroxide CuOH(HO).
J Phys Chem A
May 2021
Department of Chemistry and Henry Eyring Center for Theoretical Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
The copper hydroxide ion, CuOH, serves as the catalytic core in several recently developed water-splitting catalysts, and an understanding of its chemistry is critical to determining viable catalytic mechanisms. In spite of its importance, the electronic structure of this open-shell ion has remained ambiguous in the literature. In particular, computed values for both the thermodynamics of hydration and the vibrational signatures of the mono- and dihydrates have shown prohibitively large errors compared to values from recent experimental measurements.
View Article and Find Full Text PDFKetamine: A tale of two enantiomers.
J Psychopharmacol
February 2021
Department of Psychological Medicine, Institute of Psychiatry, Psychology and Neuroscience, King's College London, London, United Kingdom.
The discovery of the rapid antidepressant effects of the dissociative anaesthetic ketamine, an uncompetitive N-Methyl-D-Aspartate receptor antagonist, is arguably the most important breakthrough in depression research in the last 50 years. Ketamine remains an off-label treatment for treatment-resistant depression with factors that limit widespread use including its dissociative effects and abuse potential. Ketamine is a racemic mixture, composed of equal amounts of (S)-ketamine and (R)-ketamine.
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