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Fulminic acid
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<h2 id="history">History</h2> <p>This chemical was known since the early 1800s through its salts and via the products of reactions in which it was proposed to exist,<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> but the acid itself was not detected until 1966.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="structure">Structure</h2> <p>Fulminic acid was long believed to have a structure of H–O–N+≡C−. It wasn't until the 1966 isolation and analysis of a pure sample of fulminic acid that this structural idea was conclusively disproven.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> The chemical that actually has that structure, isofulminic acid (a <a href="/facts/Tautomer/ucdXGP9C">tautomer</a> of the actual fulminic acid structure) was eventually detected in 1988.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p><p>The structure of the molecule has been determined by <a href="/facts/Microwave_spectroscopy/kfc6kCh8">microwave spectroscopy</a> with the following bond-lengths - C-H: 1.027(1) <a href="/facts/Angstrom/T5mjdd97">Å</a>, C-N: 1.161(15) <a href="/facts/Angstrom/T5mjdd97">Å</a>, N-O: 1.207(15) <a href="/facts/Angstrom/T5mjdd97">Å</a>.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> <h2 id="synthesis">Synthesis</h2> <p>A convenient synthesis involves <a href="/facts/Flash_pyrolysis/jg8aj3Pm">flash pyrolysis</a> of certain <a href="/facts/Oxime/xRlPfB6K">oximes</a>. In contrast to earlier syntheses, this method avoids the use of highly explosive metal fulminates.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Beck, W.; Feldl, K. (1966). "The Structure of Fulminic Acid, HCNO". Angew. Chem. Int. Ed. Engl. 5 (8): 722–723. doi:10.1002/anie.196607221. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Wentrup, Curt; Gerecht, Bernd; Laqua, Dieter; Briehl, Horst; Winter, Hans Wilhelm; Reisenauer, Hans Peter; Winnewisser, Manfred (1981). "Organic fulminates, R-O-NC". Journal of Organic Chemistry. 46 (5): 1046–1048. doi:10.1021/jo00318a050. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Beck, W.; Feldl, K. (1966). "The Structure of Fulminic Acid, HCNO". Angew. Chem. Int. Ed. Engl. 5 (8): 722–723. doi:10.1002/anie.196607221. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Winnewisser, Manfred; Bodenseh, Hans Karl (1967). "Mikrowellenspektrum, Struktur und /-Typ-Dublett-Aufspaltung der HCNO (Knallsäure)". Z. Naturforsch. 22 a (11): 1724–1737. Bibcode:1967ZNatA..22.1724W. doi:10.1515/zna-1967-1109. S2CID 96725880. <a href="https://doi.org/10.1515%2Fzna-1967-1109" target="_blank">https://doi.org/10.1515%2Fzna-1967-1109</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Wentrup, Curt; Gerecht, Bernd; Horst, Briehl (1979). "A New Synthesis of Fulminic Acid". Angew. Chem. 18 (6): 467–468. doi:10.1002/anie.197904671. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> </ol>