Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose

• Olivier Lessard,
• Mathilde Grosset-Magagne,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2024, 20, 2442–2454, doi:10.3762/bjoc.20.208

• orbitals. Keywords: organofluorine; pyran inter-halide; solid-state conformation; solution-state conformation; Introduction Polyfluorinated pyran analogues of carbohydrates have attracted attention over the years. This class of glycomimetics has great biological potential with useful applications [1][2

• allopyranose analogues can be found in Supporting Information File 1. Our interest in the conformation of organohalogens motivated us to compare the solid-state conformation of halogenated pyrans 13–15, and 17 [24] with α-ᴅ-talose 18 [35] (Figure 3). The crystallographic data and structural refinement details

• , intramolecular F2···F3, F2···X4, and F3···X4 contacts are smaller than the sum of the Van der Walls radii [49]. Taking together, all these data clearly demonstrate that the nature of one halogen can have an impact on the solid-state conformation of halogenated pyrans. We also evaluated the Cremer–Pople ring

Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

• Yuvixza Lizarme-Salas,
• Alexandra Daryl Ariawan,
• Ranjala Ratnayake,
• Hendrik Luesch,
• Angela Finch and
• Luke Hunter

Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216

• (Figure 2), which was among the higher-energy calculated conformers of 2 (see Supporting Information File 1), bears a close resemblance to the solid-state conformation of piperine (1, Figure 1). The structure 2f has a F–C–C–F dihedral angle of 57° and a F–C–C=O dihedral angle of –133°. These angles

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• the previous minimum), a new lowest minimum very similar to the solid state conformation was detected lying 31.8 kJ/mol below the previous one. Another 5000 steps, now 15000 in total, nevertheless did not lead to a lower minimum. Hence, 10000 MC steps were chosen as total number of steps for the

• , instead of a bent conformation known from the bioactive solid-state conformation (see Supporting Information File 1, Figure S1). The OPLS-AA force field seems to underrate the attractive long-range interactions between the amidic group and the oxazolidinone ring also in the bound state. We would like to

Inversion symmetry and local vs. dispersive interactions in the nucleation of hydrogen bonded cyclic n-mer and tape of imidazolecarboxamidines

• Sihui Long,
• Venkatraj Muthusamy,
• Peter G. Willis,
• Sean Parkin and
• Arthur Cammers

Beilstein J. Org. Chem. 2008, 4, No. 23, doi:10.3762/bjoc.4.23

• state motif of 2 is likely the Ci dimer and structures that successfully compete with the Ci dimer should have increased stabilities from identifiable atomic parameters. The dihedral angles, θ, between the imidazole and the amidine moieties characterize the solid-state conformation and are reported in