Isoselenocyanates versus Isothiocyanates and Isocyanates

The Journal of Physical Chemistry. a
Anna ChrostowskaJean-Claude Guillemin

Abstract

Alkyl and aryl isoselenocyanates are well known intermediates in the synthesis of various organoselenium compounds, but the knowledge of the physicochemical properties of simple unsaturated derivatives is still fragmentary. Vinyl-, 2-propenyl-, and cyclopropyl isoselenocyanates have been prepared by reaction of selenium in powder with the corresponding isocyanides. The isoselenocyanates of this series, with a variable distance between the N═C═Se group and the unsaturated or pseudounsaturated group, have been studied by UV-photoelectron spectroscopy and quantum-chemical calculations. For each of these three isoselenocyanates, the exploration of conformers and geometrical optimization always converge toward only one local minimum. The vinyl and cyclopropyl derivatives are characterized by similar order of magnitude of interactions between the NCSe group and the substituent, while for allylic compound two noninteracting moieties should be considered. The same conclusions were obtained for vinylic and cyclopropylic sulfur and oxygen derivatives. Thus the type and extent of interactions between the N═C═X (X = O, S, Se) group and an unsaturated (vinyl, allyl, or cyclopropyl) moiety are now clarified.

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Feb 13, 2001·Journal of Molecular Spectroscopy·Anna ChrostowskaJean-Louis Ripoll
Jul 13, 2006·The Journal of Physical Chemistry. a·Virginie LemierreHenry Chermette
Sep 14, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dinesh Ramesh GarudHideharu Ishihara
Dec 17, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Anna ChrostowskaJean-Claude Guillemin
Mar 27, 2012·The Journal of Physical Chemistry. a·Harald MøllendalJean-Claude Guillemin
Aug 15, 2012·Journal of Cheminformatics·Marcus D HanwellGeoffrey R Hutchison
Nov 4, 2017·The Journal of Chemical Physics·Audrey MazièreHenry Chermette

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Citations

Jan 12, 2019·Journal of Medicinal Chemistry·Emily E FriebenArun K Sharma
Mar 1, 2019·The Journal of Physical Chemistry. a·Wenhao SunJennifer van Wijngaarden
Apr 22, 2020·The Journal of Physical Chemistry. a·Joseph StitskyJennifer van Wijngaarden

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