Study of heavy atom influence on poly-halogenated compounds using DP4/MM-DP4+/DP4+: insights and trends

Passaglia, Lucas; Zanardi, María M.; Sarotti, Ariel M.

doi:10.1039/d3ob02077k

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob02077k

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Study of heavy atom influence on poly-halogenated compounds using DP4/MM-DP4+/DP4+: insights and trends

Lucas Passaglia,

María M. Zanardi,

Ariel M. Sarotti

Abstract: Nuclear Magnetic Resonance (NMR) spectroscopy complemented by Density Functional Theory (DFT) calculations is a crucial tool for structural elucidation. Nevertheless, the precision of NMR predictions is influenced by the 'heavy...

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

Lessard,

Grosset-Magagne,

Johnson

et al. 2024

Beilstein J. Org. Chem.

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In this work, we describe the synthesis of halogenated pyran analogues of ᴅ-talose using a halo-divergent strategy from known 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-ᴅ-mannopyranose. In solution and in the solid-state, all analogues adopt standard 4C1-like conformations despite 1,3-diaxial repulsion between the F2 and the C4 halogen. Moreover, the solid-state conformational analysis of halogenated pyrans reveals deviation in the intra-annular torsion angles arising from repulsion between the axial fluorine at C2 and the axial halogen at C4, which increases with the size of the halogen at C4 (F < Cl < Br < I). Crystal packing arrangements of pyran inter-halides show hydrogen bond acceptor and nonbonding interactions for the halogen at C4. Finally, density functional theory (DFT) calculations corroborate the preference of talose analogues to adopt a 4C1-like conformation and a natural bonding orbital (NBO) analysis demonstrates the effects of hyperconjugation from C–F antibonding orbitals.

show abstract

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

Lessard,

Grosset-Magagne,

Johnson

et al. 2024

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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Study of heavy atom influence on poly-halogenated compounds using DP4/MM-DP4+/DP4+: insights and trends

Abstract: Nuclear Magnetic Resonance (NMR) spectroscopy complemented by Density Functional Theory (DFT) calculations is a crucial tool for structural elucidation. Nevertheless, the precision of NMR predictions is influenced by the 'heavy...

Cited by 1 publication

References 38 publications

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

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

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