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Science Poetry

Strained Efforts

“Three C and six H and 
Shape most triangular:
Name given sample as
Cyclopropane.
Simple example for
Nomenclatorial 
Rules, regulations.
(Ring, meter: both strained.)”

The 27 April 2022 Twitter poem focused on information related to cyclopropane as a representative hydrocarbon molecule.  

“Three C and six H and /
Shape most triangular: /
Name given sample as /
Cyclopropane…”

Cyclic hydrocarbon compounds (those that contain only carbon and hydrogen atoms) can be represented with skeletal formulas.  Given the nuances of drawing such structures, the compounds’ representations yield simple shapes.  

Cyclohexane has the molecular formula C6H12, and its skeletal structure looks like a hexagon.  Cyclopentane has the molecular formula C5H10, and its skeletal structure looks like a pentagon.  Cyclobutane has the molecular formula C4H8, and its skeletal structure looks like a square.  Cyclopropane has the molecular formula C3H6, and its skeletal structure looks like a triangle.  

Seeing a “shape most triangular” in an organic chemistry setting indicates that the molecule of interest is cyclopropane.  

“Simple example for /
Nomenclatorial /
Rules, regulations. /
(Ring, meter: both strained.)”

Each part of cyclopropane’s name describes important information, as portrayed by the “nomenclatorial rules [and] regulations” involved.  

Prop” communicates that three carbon atoms are in the structure; “ane” indicates that only single carbon-carbon bonds are present in the molecule (and thus also communicates the number of hydrogen atoms, since it is known that carbon will form four bonds overall).  “Cyclo” explains that the structure takes the shape of a ring, with the carbons circling back to bond to one another, rather than an acyclic chain. 

Cyclopropane is a “strained” structure: it is not possible for the carbon atoms in the ring to each take on the exact dimensions predicted for tetrahedral molecular geometries and still lead overall to the triangular shape.  The last line acknowledges this and also notes that the pseudo-double-dactyl poem strains a bit on its own, with an imperfect central rhyme and some metric flaws.