Nuclear Magnetic Resonance Spectroscopy. Studies of 1,1,4,4-Tetrafluoro- 1,3-alkadienes

doi:10.1021/JA01084A032

Paper

Nuclear Magnetic Resonance Spectroscopy. Studies of 1,1,4,4-Tetrafluoro- 1,3-alkadienes

Published Mar 1, 1965 · K. L. Servis, John D. Roberts

Journal of the American Chemical Society

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Abstract

1,1,4,4-Tetrafuoro-1,3-butadiene is indicated by dipole moment studies to exist in the s-trans conformation. The ^(19)F-^(19)F spin-spin coupling constants for this compound are surprisingly similar to those of bis-4,5-(difluoromethylene)cyclohexene and perfluoro-1,2-dimethylenecyclobutane, both of which substances have their double bonds held in s-cis configurations. The results are related to the mechanism of transmission of fluorine-fluorine spin-spin interactions and are inconsistent with a predominance of a "through-space" mechanism of coupling.

Study Snapshot

1,1,4,4-Tetrafuoro-1,3-butadiene has a similar spin-spin coupling constant to bis-4,5-(difluoromethylene)cyclohexene and perfluoro-1,2-dimethylenecyclobutane, suggesting a "

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Nuclear Magnetic Resonance Spectroscopy. Studies of 1,1,4,4-Tetrafluoro- 1,3-alkadienes

References

Citations

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Hydrofluoronickelacycles from Ni(0) complexes with trifluoroethylene show three predominant isomers, with phosphine size influencing the ratio of these isomers.

Synthesis and properties of the strained alkene perfluorobicyclo[2.2.0]hex-1(4)-ene.

The strained alkene perfluorobicyclo[2.2.0]hex-1(4)-ene is a stable, highly reactive fluoroalkene with high yield and purity.

Evidence for “through‐space” long‐range proton‐proton coupling in acetone

"Through-space" long-range proton-proton coupling in acetone may explain the observed trend, suggesting a better numerical fit.

Synthesis of fluorinated dienes by palladium-catalyzed coupling reactions.

Palladium-catalyzed coupling reactions enable the synthesis of partly fluorinated 1,3- and 1,4-dienes on a laboratory scale, with structures elucidated by X-ray crystallography.

Unusual long-range spin-spin coupling in fluorinated polyenes: a mechanistic analysis.

Fluorinated polyenes show unusual long-range spin-spin coupling, dominated by the spin-dipole term, providing guidelines for designing suitable active molecules for NMR quantum computers.

Internal rotations in the difluorobutadiene and tetrafluorobutadiene molecules: a DFT B3LYP study

The s-trans conformers are more stable in difluorobutadiene and tetrafluorobutadiene molecules, with the exception of 1,2,3,4-TFBD, where the s-gauche conformer is slightly more stable.

Theoretical Studies of Geometries of Hexafluoro-1,3-butadiene, Tetrafluoro-1,3-butadiene, and Difluoro-1,3-butadiene Compounds

The geometrical structures of hexafluoro-1,3-butadiene, tetrafluoro-1,3-butadiene, and difluoro-1,3-butadiene compounds are influenced by steric repulsion between fluorine atoms, hydrogen