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Carbonyl Diisocyanate CO(NCO)2: Synthesis and Structures in Solid State and Gas Phase
Thomas M Klapötke1, Burkhard Krumm1, Sebastian Rest1
1Ludwig-Maximilians Universität München , Department Chemie, Butenandtstraße 5-13(D), 81377 München, Germany.
The Journal of Physical Chemistry. A
|June 25, 2016
Summary
A new synthesis for carbonyl diisocyanate, CO(NCO)2, was developed. Its structure was determined in solid and gas phases using X-ray diffraction, electron diffraction, and quantum-chemical calculations, confirming the syn-syn conformation as most stable.
Area of Science:
- Chemistry
- Physical Chemistry
- Materials Science
Background:
- Carbonyl diisocyanate (CO(NCO)2) is a reactive compound with limited structural data.
- Existing synthesis methods may have limitations in yield or purity.
Purpose of the Study:
- To develop a modified synthesis for carbonyl diisocyanate (CO(NCO)2).
- To characterize the structure of CO(NCO)2 in the solid state, gas phase, and for single molecules.
- To determine the lowest energy conformation and identify other conformers.
Main Methods:
- Synthesis using trichloroisocyanuric acid and diphosgene.
- Nuclear Magnetic Resonance (NMR) spectroscopy ((13)C and (15)N).
- X-ray diffraction (XRD) on in situ grown crystals.
- Gas Electron Diffraction (GED).
- Quantum-chemical calculations.
Main Results:
- A modified synthesis route for CO(NCO)2 was established.
- First-time determination of the (15)N NMR shift for CO(NCO)2.
- Structural determination in the solid state (XRD) and gas phase (GED).
- Quantum-chemical calculations predicted and confirmed the syn-syn conformation as the most stable.
- GED and theoretical calculations identified the presence and structure of a syn-anti conformer.
Conclusions:
- The syn-syn conformation is the most energetically favorable for CO(NCO)2.
- The study provides a comprehensive structural analysis of CO(NCO)2 across different phases.
- The developed synthesis offers a new route for accessing this important isocyanate compound.
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