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Isoselenocyanates versus Isothiocyanates and Isocyanates
Anna Chrostowska1, Clovis Darrigan1, Alain Dargelos1
1Université de Pau et des Pays de l'Adour, CNRS, UMR 5254 IPREM, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux , 64000 Pau , France.
The Journal of Physical Chemistry. A
|February 28, 2018
Summary
Researchers explored unsaturated isoselenocyanates, clarifying interactions between the NCSe group and unsaturated moieties. This advances understanding of organoselenium compound synthesis and properties.
Area of Science:
- Organoselenium Chemistry
- Spectroscopy
- Computational Chemistry
Background:
- Alkyl and aryl isoselenocyanates are key intermediates in organoselenium synthesis.
- Physicochemical properties of simple unsaturated isoselenocyanates remain incompletely understood.
Purpose of the Study:
- To synthesize and characterize vinyl-, 2-propenyl-, and cyclopropyl isoselenocyanates.
- To investigate the electronic interactions within these molecules using UV-photoelectron spectroscopy and quantum-chemical calculations.
Main Methods:
- Synthesis of isoselenocyanates via reaction of selenium powder with isocyanides.
- UV-photoelectron spectroscopy for electronic structure analysis.
- Quantum-chemical calculations for geometrical optimization and conformer exploration.
Main Results:
- A single stable conformer was identified for each studied isoselenocyanate.
- Vinyl and cyclopropyl derivatives exhibit significant interaction between the NCSe group and the substituent.
- Allylic derivatives consist of two non-interacting moieties.
Conclusions:
- The study clarifies the nature and extent of interactions between the N═C═X (X = O, S, Se) group and unsaturated moieties (vinyl, allyl, cyclopropyl).
- Findings are consistent across analogous sulfur and oxygen compounds, providing a broader understanding of these functional groups.
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