On the Nature of C-H⋅⋅⋅F-C Interactions in Hindered CF3-C(sp3) Bond Rotations

• In cinchona alkaloid-based scaffolds, hindered CF3 rotations have been observed. The variation in barrier heights for the CF3 rotations is controlled by the corresponding entropic changes when the substituents are changed from an allyl to a bulky 9-methylanthracenyl group. Quantum chemical and experimental studies have shown that the noncovalent C3′[BOND]H1⋅⋅⋅F[BOND]C interactions in the studied cases possess a weak hydrogen bonding-like

Ämnesord

NATURVETENSKAP  -- Kemi -- Teoretisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

hydrogen bonding

cinchona alkaloids

steric hindrance

conformational isomerism

fluorine

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