Solvent polarity effects on carbene/ether-O-ylide equilibria

The Journal of Physical Chemistry. a
Pablo A HoijembergKarsten Krogh-Jespersen

Abstract

p-Nitrophenylchlorocarbene (PNPCC) reacted reversibly with tetrahydrofuran (THF), tetrahydropyran (THP), 1,3-dioxane (1,3-D), and 1,4-dioxane (1,4-D) to form O-ylides 8, 9, 10, and 11, respectively. The O-ylides were visualized by their characteristic UV-vis spectroscopic signatures. Equilibrium constants (K) were determined spectroscopically, and studies of K as a function of pentane/1,2-dichloroethane (DCE) solvent blends illustrated the dependence of K on solvent polarity. Electronic structure calculations based on density functional theory provided carbene/ether O-ylide structures and energetics, as well as electronic spectroscopic parameters for use in the determination of K. Comparisons of the computed and experimental data were generally satisfactory.

References

Mar 30, 2007·Journal of the American Chemical Society·Robert A MossKarsten Krogh-Jespersen
Apr 25, 2008·The Journal of Physical Chemistry. a·Robert A MossKarsten Krogh-Jespersen
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Aug 5, 2010·Journal of the American Chemical Society·Robert A MossKarsten Krogh-Jespersen
Aug 31, 2011·The Journal of Physical Chemistry. B·Raphael F RibeiroDonald G Truhlar
Dec 20, 2011·The Journal of Physical Chemistry. a·Pablo A HoijembergKarsten Krogh-Jespersen

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Citations

Jun 27, 2013·Photochemistry and Photobiology·Robert A MossKarsten Krogh-Jespersen
Nov 17, 2015·Physical Chemistry Chemical Physics : PCCP·Sara GómezC Z Hadad
Aug 6, 2014·The Journal of Physical Chemistry. a·Pablo A HoijembergKarsten Krogh-Jespersen

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