The bellamy relationship and the nature of the H-bond. 2-Haloethanols

Вокин, А. И.; Turchaninov, V. K.

doi:10.1134/s0030400x15010269

Cited by 3 publications

(1 citation statement)

References 32 publications

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“…In this work, we present a study of the geometrical structure and energetics of clusters of 1ClEtOH and 2ClEtOH with n water molecules (n = 1‐4). While 2ClEtOH has been studied several times and is well known, much less information exists in the literature about the 1ClEtOH isomer, which nonetheless may play some important role in the dehalogenation path of 2ClEtOH.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of the microhydration of 1‐chloro and 2‐chloro ethanol as a clue for their relative propensity toward dehalogenation

Petsis

Salta

Kosmas

et al. 2019

Int J of Quantum Chemistry

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In e25931, Oscar Ventura and coworkers describe micro-hydration of 1-chloro and 2-chloroethanol. They considered hydration patterns that mimic the interaction of the molecules with small ice clusters since the 2-chloroethanol is a precursor of vinyl alcohol involved in atmospheric and interstellar reactions. By the explicit inclusion of up to 4 water molecules, the study determined the effect of hydration on the C-Cl bond length and the IR spectrum of both isomers, finding that water complexation affects differently the C-Cl bond of the 2 molecules.

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Section: Introductionmentioning

confidence: 99%

Theoretical study of the microhydration of 1‐chloro and 2‐chloro ethanol as a clue for their relative propensity toward dehalogenation

Petsis

Salta

Kosmas

et al. 2019

Int J of Quantum Chemistry

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The Fluorine gauche Effect and a Comparison with Other Halogens in 2‐Halofluoroethanes and 2‐Haloethanols

Martins

Freitas

2019

Eur J Org Chem

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While the gauche effect in 1,2‐difluoroethane is widely known as being due to hyperconjugative interactions between σCH electron‐donating orbitals and σ*CF electron‐accepting orbitals, the corresponding 1,2‐dichloro, 1,2‐dibromo, and 1,2‐diiodo derivatives are preferentially in the anti conformation. 2‐Halofluoroethanes (F‐CH2‐CH2‐X) combine a small halogen (fluorine) and a vicinal low‐lying energy antibonding orbital (σ*CX) that activates a stabilizing antiperiplanar σCH → σ*CX electron delocalization, which can induce the gauche effect. On the other hand, σCX orbitals are good electron donors to σ*CF, that would favor an “anti effect”, in addition to traditional interpretations based on steric and electrostatic repulsion. Therefore, a balance of steric, dipolar and hyperconjugative effects drive the conformational equilibrium of these compounds – hyperconjugation was found to explain the gauche effect in some cases, whilst Lewis‐type interactions determine the anti preference in others. The gauche effect takes place in a polar solvent, but not for 1‐fluoro‐2‐iodoethane. According to NMR three‐bond spin‐spin coupling constants, the gauche population increases when fluorine is replaced by a hydroxyl group (except for 2‐fluoroethanol relative to 1,2‐difluoroethane), but this is not primarily due to intramolecular hydrogen bond.

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FIR spectroscopy and DFT calculations involving 2-chloroethanol: Analysis of the ν19 + ν21←ν21 torsional hot band, and the solvated substitution reaction between ethylene glycol and hydrogen chloride

Hull

Soliday

2020

Journal of Molecular Structure

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The bellamy relationship and the nature of the H-bond. 2-Haloethanols

Cited by 3 publications

References 32 publications

Theoretical study of the microhydration of 1‐chloro and 2‐chloro ethanol as a clue for their relative propensity toward dehalogenation

Theoretical study of the microhydration of 1‐chloro and 2‐chloro ethanol as a clue for their relative propensity toward dehalogenation

The Fluorine gauche Effect and a Comparison with Other Halogens in 2‐Halofluoroethanes and 2‐Haloethanols

FIR spectroscopy and DFT calculations involving 2-chloroethanol: Analysis of the ν19 + ν21←ν21 torsional hot band, and the solvated substitution reaction between ethylene glycol and hydrogen chloride

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