ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Using a combination of mass spectrometric techniques, it is shown that 5-amino-4-cyanoisoxazole molecular ions (1+·), lose isocyanic acid HN=O, not fulminic acid, HC≡N → O. Metastable ion fragmentations (unimolecular and collision induced) and deuterium-labelling experiments are in agreement with the formation of a cumulenic structure, HN=C=C=C=NH (3a+·). The hitherto unreported molecules HNCCCNH are also shown to be stable when formed in the low-pressure gas phase of the mass spectrometer by using the technique of neutralization-reionization mass spectrometry. The arguments developed for the characterization of 3a+· have also been extended to the methylated and phenylated analogues 3b+· and 3c+· [RN=C=C=C=NH+·, R = CH3 or C6H5]. On flash-vacuum pyrolysis at 700°C, 1 also loses HN=C=O producing the cumulene 3a, which is in turn readily tautomerized into malononitrile via wall collisions.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210281030
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