Chemical nomenclature, replete as it is with compounds with complex names, is a repository for some very peculiar and sometimes startling names. A browse through the Physical Constants of Organic Compounds in the CRC Handbook of Chemistry and Physics (a fundamental resource) will reveal not just the whimsical work of chemists, but the sometimes peculiar compound names that occur as the consequence of simple juxtaposition. Some names derive legitimately from their chemical makeup, from the geographic region where they may be found, the plant or animal species from which they are isolated or the name of the discoverer.
Some are given intentionally unusual trivial names based on their structure, a notable property or at the whim of those who first isolate them. However, many trivial names predate formal naming conventions. Trivial names can also be ambiguous or carry different meanings in different industries, geographic regions and languages.
Godly noted that "Trivial names having the status of INN or ISO are carefully tailor-made for their field of use and are internationally accepted". In his preface to Chemical Nomenclature, Thurlow wrote that "Chemical names do not have to be deadly serious". A website in existence since 1997 and maintained at the University of Bristol lists a selection of 'molecules with silly or unusual names' strictly for entertainment. These so-called silly or funny trivial names (of course depending on culture) can also serve an educational purpose. In an article in the Journal of Chemical Education, Dennis Ryan argues that students of organic nomenclature (considered a 'dry and boring' subject) may actually take an interest in it when tasked with the job of converting funny-sounding chemical trivial names to their proper systematic names.
The collection listed below presents a sample of trivial names and gives an idea how chemists are inspired when they coin a brand new name for a chemical compound outside of systematic naming. It also includes some examples of systematic names and acronyms that accidentally resemble English words.
Glenn Seaborg told his students that he proposed the chemical symbol Pu (from P U) instead of the conventional "Pl" for plutonium as a joke, only to find it officially adopted. Unununium (Uuu) was the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.
A class of compounds with a 'window pane motif' (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fusedcarbocycles centred on a quaternary carbon resulting a twice over spiro compound. The illustration at right shows a generic fenestrane as well as the specific examples [4,4,4,4]fenestrane and [5,5,5,5]fenestrane. Fenestranes are of considerable interest in theoretical chemistry though comparatively few have actually been synthesised.
A close relative to adamantane and its proper name is ethano-bridged noradamantane. Because its unusual ethano-bridge was a deviation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child.
A strongly oxidizing mixture of hydrogen peroxide and sulfuric acid used to remove organic residues from substrates and glassware. The name refers to the voracious appetite of the Amazonian piranha fish.
^Zimmerman, Howard E.;; Robert M. Paufler. "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical Society82 (6): 1514–1515. doi:10.1021/ja01491a071.
^Verbrugge, P. A. (1977). "Unusual organic compounds. XXIV. Compounds with the formula (CH)n. (d). Synthesis of cubane, (CH)8; homocubanes". Chemie en Techniek (Amsterdam)32 (4): 120–123.
^G. Märkl and H. Hauptmann (1983-06-14). "Untersuchungen zur Chemie der Arsole 1,1-dichlor-1-R-λ5-arsole-1-chlorarsole 2,2′,5,5′-tetraphenyldiarsolyl (Studies on the chemistry of arsoles)". J. Organomet. Chem.248 (3): 269–285. doi:10.1016/S0022-328X(00)98709-6.
^R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
^Apitz-Castro R, Béguin S, Tablante A, Bartoli F, Holt JC, Hemker HC (1995). "Purification and partial characterization of draculin, the anticoagulant factor present in the saliva of vampire bats (Desmodus rotundus)". Thromb. Haemost.73 (1): 94–100. PMID7740503.
^Charles O, Coolsaet B (1972). "[Prevention of hemorrhage in prostatic surgery. Apropos of the study of the hemostatic activity in prostatectomy of a new molecule: beta-naphthoquinone monosemicarbazone (Naftazone)]". Annales d'urologie (in French) 6 (3): 209–212. PMID4562066.
^Hogness, T.; Lunn, E. (1925). "The Ionization of Hydrogen by Electron Impact as Interpreted by Positive Ray Analysis". Physical Review26 (1): 44–55. doi:10.1103/PhysRev.26.44.
^Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+−.)-hirsutene Dennis P. Curran and Donna M. Rakiewicz J. Am. Chem. Soc.; 1985; 107(5) pp 1448 – 1449; doi:10.1021/ja00291a077
^Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis Shigeo Nozoe, Jun Furukawa, Ushio Sankawa and Shoji Shibata Tetrahedron Letters Volume 17, Issue 3 , January 1976, Pages 195–198 doi:10.1016/0040-4039(76)80013-5
^"Jesterone and hydroxy-jesterone antioomycete cyclohexenone epoxides from the endophytic fungus Pestalotiopsis jesteri" Jia Yao Li and Gary A. Strobel, Phytochemistry, 57 (2001) 261–265
^SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
Alex Nickon and Ernest F. Silversmith, "Organic Chemistry, the Name Game: Modern Coined Terms and Their Origins", Pergamon 1987. ISBN 0-08-034481-X.
Randall, David (February 1, 2004). "Storyville: Molecular scientists have a word for it". The Independent on Sunday (London, England).(subscription required)
Wallechinsky, David; Wallace, Amy (2005). "24. Molecules and amoebas with funny names". The new book of lists : the original compendium of curious information. New York, N.Y.: Canongate. pp. 203–205. ISBN9781841957197.