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Title: Synthesis, Spectroscopy and Structure of the Parent Furoxan (HCNO)(2)
Authors: Pasinszki, Tibor
Havasi, Balazs
Hajgato, Balazs
Westwood, Nicholas P. C.
Issue Date: 2009
Citation: JOURNAL OF PHYSICAL CHEMISTRY A, 113(1). p. 170-176
Abstract: The parent furoxan (1,2,5-oxadiazole 2-oxide), synthesized from glyoxime and NO2(g), has been investigated in the gas phase for the first time by mid-infrared and He I photoelectron spectroscopy, and in the liquid phase by Raman spectroscopy. The ground-state geometry has been obtained from quantum-chemical calculations at the B3LYP, MPn (n = 2-4), CISD, QCISD, CCSD, CCSD(T), RSPTn (n = 2,3), MRCI, and MR-AQCC levels using 6-311++G(2d,2p), cc-pVTZ, aug-cc-pVTZ, cc-pCVTZ, and cc-pVQZ basis sets. Furoxan is predicted to be planar, with a strong exocyclic and a relatively weak endocyclic N-O bond. The furoxan moiety is electron rich, indicated e.g. by a large negative NPA charge (-0.46 e). According to various aromaticity indices, furoxan is nearly as aromatic as furan and furazan. Unlike alkyl- and cyano-substituted furoxans, the parent furoxan, upon thermolysis, does not cleave to the monomer nitrile oxide, yielding only HNCO, HCN, CO2, CO, NO, and H2O decomposition products.
Notes: [Pasinszki, Tibor] Lorand Eotvos Univ, Dept Inorgan Chem, Inst Chem, H-1117 Budapest, Hungary. [Pasinszki, Tibor; Havasi, Balazs] Budapest Univ Technol & Econ, Dept Inorgan Chem, H-1521 Budapest, Hungary. [Hajgato, Balazs] Hasselt Univ, Dept SBG, B-3590 Diepenbeek, Belgium. [Westwood, Nicholas P. C.] Univ Guelph, Guelph Waterloo Ctr Grad Work Chem, Dept Chem, Guelph, ON N1G 2W1, Canada.
URI: http://hdl.handle.net/1942/9207
DOI: 10.1021/jp810066r
ISI #: 000262140100023
ISSN: 1089-5639
Category: A1
Type: Journal Contribution
Validation: ecoom, 2010
Appears in Collections: Research publications

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