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The story of the discovery, investigation, and eventual correct formulation
of fulminic acid, HCNO, extends over a period of 200 years and reflects
uniquely, in its many stages, the evolution of organic chemistry from
post-alchemistic times to the age of wave mechanics. Fulminic acid was
discovered in 1800 when E. Howard serendipitously prepared its highly
explosive mercury and silver salts. The determination of its structure
presented unusual difficulties and taxed the ingenuity of leading chemists
of successive generations. Their work generated a procession of proposed
and discarded formulations that was only finally ended in the 1960s with
the recognition of fulminic acid as the mesomeric structure
and hence with its identification as the parent compound of the important
class of the nitrile N-oxides. Recently fulminic acid and several of its
isotopomers have been subjected to the most searching spectroscopic
investigations and ab initio computations, by which its molecular
dimensions and geometry, and its "quasi-linear" structure have been
revealed. In technology, mercury fulminate occupied for nearly a century a
uniquely important position as the only available practical detonator for
every kind of conventional explosive.
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