Not all carbon—carbon bonds are equivalent: anomeric effect of sp-hybridized carbon atom

Vatsadze, S. Z.; Medved’ko, A. V.; Mirakbarov, M. Kh.; Minyaev, M. E.; Khrustalev, V. N.; Zaripov, D. U.; Medvedev, M. G.; Alabugin, I. V.

doi:10.1007/s11172-024-4143-8

Cited by 1 publication

(3 citation statements)

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“…The protonated syn−anti species is the more stable conformer because in addition to the strong anomeric effect, the cation is stabilized by the SSE . The sp 2 -hybridized carboxylic carbon atom stabilizes the anomeric effect due to the increased electron deficiency in protonation . The literature reported the strengthening influence of the triple bond on the anomeric effect .…”

Section: Theoretical Calculationsmentioning

confidence: 99%

“…29 The sp 2 -hybridized carboxylic carbon atom stabilizes the anomeric effect due to the increased electron deficiency in protonation. 30 The literature reported the strengthening influence of the triple bond on the anomeric effect. 30 However, the protonation is carried out in the protic solvent HF.…”

Section: ■ Theoretical Calculationsmentioning

confidence: 99%

“…30 The literature reported the strengthening influence of the triple bond on the anomeric effect. 30 However, the protonation is carried out in the protic solvent HF. The protic solvent causes the anti conformation to lose proportion because hydrogen bonds stabilize the less favorable syn−syn conformation more strongly.…”

Section: ■ Theoretical Calculationsmentioning

confidence: 99%

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Synthesis and Structure of Protonated Propiolic Acid

Hollenwäger,

Thamm,

Bockmair

et al. 2024

J. Org. Chem.

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Propiolic acid was investigated in the superacidic system XF/SbF 5 (X = H, D). The salts of the monoprotonated species of propiolic acid were characterized by vibrational and NMR spectroscopy as well as single-crystal analyses. The rotational conformers of the protonated species can be distinguished by NMR spectroscopy via the temperature-dependent rotational barrier. In the solid state, they can be detected by H/D exchange and packing effects due to different anions. The experimental results are discussed together with an IRC calculation of the rotational barrier. After acetic acid and formic acid, this is the third protonated carboxylic acid for which the energy differences between the conformers have been determined.

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Section: Theoretical Calculationsmentioning

confidence: 99%