Tuesday 7 April 2015

nomenclature - Etymology of saturation degrees (-ane, -ene, -yne) in aliphatic compounds


I like to know where the names for saturated, unsaturated double, and unsaturated triple bonded aliphatic compounds came from.


What is the reason/etymology behind the suffix -ane, -ene, and -yne?


I suppose it parallels something like the inflection-based umlauts in Germanic languages (which may be seen rudimentary in modern English for example in words like mouse/mice) but that is utter speculation. Yet I did not find anything in the web (I think some good extensive Chemical Etymological Encyclopaedia is really missing).




Answer



I found the following information through a website linked to Yale University.


The naming structure seems to have evolved from some of the early nonsystematic names given to hydrocarbons. It started with Dumas who in 1835 came up with the name Methylene for the $\ce{CH2}$ radical. The "-ene" suffix is a Greek feminine patronymic which was used to denote that Methylene was the "daughter of" (derived from) the "spirit of wood" or what we now call methanol (Dumas believed methanol had the formula $\ce{CH2\cdot H2O}$).


The naming structure caught on for ethylene since it was related to ethyl(even though the meth- in Methylene came from a Greek work for wine and not the numerical prefix used in methyl).


When the use of these feminine patronymics (-ene, -ine, -one) became common during the 1860s, Hoffman proposed making a consistent nomenclature that followed the standard progression of vowels: a e i o u. This led to the suffixes -ane, -ene, -ine(-yne), -one, and -une to refer to increasingly unsaturated hydrocarbons.


Since -one was already in use for ketone structures, only the first three suffixes caught on.


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