F···HO intramolecular hydrogen bond as the main transmission mechanism for 1hJF,H(O) coupling constant in 2′‐fluoroflavonol

@article{Fonseca2012FHOIH,
  title={F···HO intramolecular hydrogen bond as the main transmission mechanism for 1hJF,H(O) coupling constant in 2′‐fluoroflavonol},
  author={T{\^a}nia A O Fonseca and Teodorico Castro Ramalho and Matheus P. Freitas},
  journal={Magnetic Resonance in Chemistry},
  year={2012},
  volume={50}
}
Flavonoids are useful compounds in medicinal chemistry and exhibit conformational isomerism, which is ruled by intramolecular interactions. One of the main intramolecular forces governing the stability of conformations is the hydrogen bond. Hydrogen bond involving fluorine covalently bonded to carbon has been found to be rare, but it appears in 2′‐fluoroflavonol, although the F···HO hydrogen bond cannot be considered the main effect governing the conformational stability of this compound… 
6 Citations

Intramolecular OH···FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2.

An intramolecular bifurcated H-bond from the axial HO-2 group to the axial F-4 atom and to the O5 atom of α-D-hexopyranosides in apolar solvents is evidenced in (1)H NMR spectra. The H-accepting

Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring

Density functional theory studies at the B3LYP/6-311++G(d,p) level were carried out on these compounds and on four non-fluorinated derivatives, allowing to calculate geometries, tautomeric energies and ring-inversion barriers, that were compared with the experimental results obtained by static and dynamic NMR in solution and in solid state.

Applications of Fluorine in Medicinal Chemistry.

The effects of the strategic incorporation of fluorine in drug molecules and applications in positron emission tomography are provided, as well as new synthetic methodologies that allow more facile access to a wide range of fluorinated compounds.

Tactical Applications of Fluorine in Drug Design and Development

The increasing utilization of fluorine in drug design parallels advances in understanding the physicochemical attributes of this element and an enhanced appreciation of how these unique properties

Modern quantum chemical methods for calculating spin–spin coupling constants: theoretical basis and structural applications in chemistry

The modern quantum chemical methods for calculating spin–spin coupling constants in NMR spectra are reviewed. The theoretical basis of these methods and author's vision of the prospects of their

Gauche preference of β-fluoroalkyl ammonium salts.

The strong gauche preference in 3-fluoropiperidinium cation and analogues, in the gas phase, is dictated by electrostatic interactions, which can be both hydrogen bond F···H(N(+)) and F/N(+) attraction.

References

SHOWING 1-10 OF 37 REFERENCES

Structure, Conformations, and Internal Hydrogen Bonding in Gaseous 4-Fluorobutan-1-ol. Gas-Phase Electron Diffraction and Ab Initio Study

Excluding enantiomers, there are 14 possible rotomeric conformations of 4-fluorobutan-1-ol, of which two are capable of forming an internal O−H···F hydrogen bond. The composition of the gaseous

1hJFH coupling in 2‐fluorophenol revisited: Is intramolecular hydrogen bond responsible for this long‐range coupling?

The present study shows that a hydrogen bond between the OH group and the fluorine atom is not involved in the 1hJFH spin–spin coupling transmission either for 4‐bromo‐2‐fluorophenol or

Theoretical Study of the Effect of Hydrogen-Bonding on the Stability and Vibrational Spectrum of Isolated 2,2,2-Trifluoroethanol and Its Molecular Complexes

The structural and spectroscopic effects of hydrogen bonding on isolated 2,2,2-trifluoroethanol (TFE) and its molecular complexes are theoretically investigated at the MP2/aug-cc-pVDZ level. As a

A DFT and AIM analysis of the spin–spin couplings across the hydrogen bond in the 2‐fluorobenzamide and related compounds

D density functional theory (DFT) calculations are provided that justify the existence of a weak HB in the absence of solvent, while solvents that act as HB acceptors break down the intramolecular hydrogen bond (IMHB) of 2‐fluorobenzamide.

Inter- and intramolecular hydrogen bonds in polyamines: variable-concentration 1H-NMR studies

Inter- and intramolecular hydrogen bonding play an important role in determining the arrangement, physical properties, and reactivity of a great diversity of structures in chemical and biological

Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols

The conformer stabilities of 2'-haloflavonols were found to be dictated mainly by a C=O···H–O intramolecular hydrogen bond, but an unusual C–F··· H–O hydrogen-bond and intramolescular C–X···O nonbonding interactions are also present in such compounds.

Effect of electronic interactions on NMR 1J(CF) and 2J(CF) couplings in cis- and trans-4-t-butyl-2-fluorocyclohexanones and their alcohol derivatives.

The PSO term of (2)J(CF) SSCC in cis-4-t-butyl-2-fluorocyclohexanone is rationalized as transmitted in part by the superposition of the F and O electronic clouds.

Thermal and solvent effects on NMR indirect spin-spin coupling constants of a prototypical Chagas disease drug.

This work has applied density functional theory (DFT) to compute the NMR (n)J(N,H) scalar couplings of a prototypical Chagas disease drug (metronidazole), highlighting the importance of properly incorporating thermal and solvent effects into NMR calculations in the condensed phase.

Experimental, SOPPA(CCSD), and DFT analysis of substitutent effects on NMR 1JCF coupling constants in fluorobenzene derivatives.

A possible method to determine experimentally a significant PSO contribution to (1)J(CF) SSCCs is discussed, and a set of consistent approximations are introduced in order to analyze the behavior of occupied and virtual orbitals.

Qualitative and quantitative measurements of hydrogen bond mediated scalar couplings in acyclic 1,3-diols.

A theoretical investigation confirmed the importance of the hydrogen bond in mediating the spin-spin coupling in these systems and observed acyclic syn- and anti-1,3-diols.