March 5, 2024The Journal of Organic ChemistryOpen Access

Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes

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Authors

MHMengfan HeShanghai Center for Brain Science and Brain-Inspired Technology BPBruno A. PiscelliUniversity of St Andrews RCRodrigo A. CormanichUniversidade Estadual de Campinas (UNICAMP)

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Implication

Conformational analysis demonstrates axial conformer preferences in halogenated cyclohexanes, indicating nonclassical hydrogen bonding governs stereochemical stability.

Key Points

Axial conformers show unexpected thermodynamic stability with a ΔG preference of 1.06 kcal mol–1 in trifluorocyclohexane, opposing standard conformational equilibria norms.
VT-NMR spectroscopy and M06-2X/aug-cc-pVTZ level computational analysis evaluated halogenated rings, while natural bond orbital analysis dissected hyperconjugation.
Highlights how nonclassical hydrogen bonding and electrostatic interactions drive axial bias, which enables predictable stereochemical control in organofluorine design.

Cite This Study

He et al. (2024) studied this question.

synapsesocial.com/papers/68e75a00b6db6435876d0e04 https://doi.org/10.1021/acs.joc.3c02868

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Implication

Conformational analysis demonstrates axial conformer preferences in halogenated cyclohexanes, indicating nonclassical hydrogen bonding governs stereochemical stability.

Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes

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Implication

Key Points

Cite This Study

Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes

Discussion

Member takes

Implication

Key Points

Cite This Study

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