Categories
Science Poetry

Total Synthesis

Deftly, inventively,
Percy L. Julian 
(Born on this date in 1899)
Works at his lab bench with
Techniques organic on
Corticosteroids’
Synthetic design.  

The 11 April 2020 Twitter poem celebrated the birthdate of Percy Julian, an organic chemist who made key insights into the structures and syntheses of many important compounds.  The same caveats I’ve used with respect to both structure and content in the last few entries certainly apply here as well.  While the metric feet are dactylic, this poem is not a true double dactyl, since it consists of seven lines rather than eight.  Moreover, Percy Julian’s story deserves much more attention than this brief verse.  In particular, I’ve mentioned the excellent NOVA episode “Forgotten Geniuselsewhere in this space and would echo that recommendation here.    

“Deftly, inventively, /
Percy L. Julian /
(Born on this date in 1899)”
Percy Lavon Julian (1899- 1975) was an organic chemist who developed several innovative synthetic routes, “deftly [and] inventively” identifying laboratory-based pathways to natural compounds known to be medicinally valuable.  Julian was the first Black chemist named to the National Academy of Sciences and was a civil rights advocate throughout his career.        

“Works at his lab bench with /
Techniques organic on /
Corticosteroids’ /
Synthetic design.”

In 1935, Julian worked with his research colleague Josef Pikl to synthesize physostigmine: a compound known for its value in the treatment of glaucoma. Physostigmine had been previously available only from the Calabar bean.  Given the relative scarcity of the natural source, it was not used as widely as a medication as it could have been if it were synthetically available: if it could be made in a lab.  

Since the natural compound had been isolated previously (and its structure was thus known), Julian developed the “total synthesis” of physostigmine: a complete route via which a chemist could start from materials available in the laboratory and arrive at the correct target compound.  Julian tested the properties of the compound synthesized in the lab against the known properties of the natural compound to verify that the synthesis was successful.  This was a momentous achievement; the laboratory at DePauw University at which Julian developed the synthesis was designated a National Historic Chemical Landmark.  

Physostigmine’s total synthesis was only one of many innovative pathways that Julian developed in his career.  His work increased the accessibility and affordability of several medicinally important compounds, many of which could be classed as “corticosteroids” (a term that lends itself particularly well to dactylic meter!).

Categories
Science Poetry

Air of Mystery

“Skillfully, quill-fully:
Madame Lavoisier,
Translating chemistry, 
Husband at side…
Pair works in tandem;
Dephlogisticated air
Named now as oxygen,
Demystified.” 

The 8 April 2020 poem was another scientific biography in shorthand, recounting a famous discovery of the Lavosiers (Antoine and Marie-Anne Lavoisier), two landmark figures in the history of chemistry.      

“Skillfully, quill-fully: /
Madame Lavoisier, /
Translating chemistry, / 
Husband at side…”
Antoine-Laurent de Lavoisier (1743-1794) is renowned as a major figure in the Chemical Revolution: the shift of chemistry towards more systematic investigations.  Often mentioned as a sidenote in chemical histories is the fact that his wife, Marie-Anne Paulze Lavoisier (1758-1836) was herself a scientist; indeed, she translated the scientific documents that facilitated many of her husband’s discoveries (presumably, with a quill!).  This seems worthy of more than a passing comment, and this poem attempts to address that humorously.      

“Pair works in tandem; /
Dephlogisticated air /
Named now as oxygen, /
Demystified.” 
The Lavoisiers’ chemistry insights were many; this poem focuses on one.  The phlogiston theory had been the prevailing understanding of combustion prior to the Lavoisiers’ work.  This theory postulated that combustible materials contained phlogiston, which was released when they burned.  Several scientists, among them English chemist Joseph Priestly, used the phlogiston theory to rationalize aspects of combustion.  The Lavoisiers, through a series of rigorous quantitative experiments, showed that combustion was instead explained by the oxygen theory: when a sample reacts with oxygen, it undergoes combustion, yielding an oxidized product.  

What Joseph Priestly had isolated and referred to as “dephlogisticated air” was thus clarified to be “oxygen,” and the element was named as such by Antoine Lavoiser.  This chemical insight was aided greatly by the work of Marie-Anne Lavoisier, who had the scientific knowledge and language fluency to translate key research articles into French so that her husband could read them.   

The compelling story of oxygen’s isolation and characterization has been told in much greater detail by other writers!  These lines focus on the unique chemistry of the Lavoisiers themselves, highlighting their collaborative research process.  

Categories
Science Poetry

Being Spontaneous

“Quietly, mightily,
Josiah Willard Gibbs
Formulates concepts for 
STEM fields galore. 
Physical, chemical
Thermodynamical
Tools: spontaneity 
Can be explored.”

Not all of the April 2020 poems were chemistry-focused, so I’ll shift ahead to the next one that was, posted on 6 April 2020.  As highlighted in the hashtags, this was the first poem in a week of “Twitter bios,” in which short biographies of scientists were presented in the double-dactyl poetic form.  In this stringent form, one of the lines should be a single word that is a double dactyl in itself.  While not all of the poems from this week managed this, this first one did, highlighting “thermodynamical” in the sixth line.   

“Quietly, mightily, /
Josiah Willard Gibbs /
Formulates concepts for / 
STEM fields galore.”
Josiah Gibbs was a scientist who made enormous contributions to several scientific fields, “formulat[ing] concepts for STEM fields galore.”   One of his most famous papers was “On the Equilibrium of Heterogeneous Substances”; however, his choice of journal was an obscure one (Transactions of the Connecticut Academy of Arts and Sciences), which meant it took several years for the impact of his important work to reach an appropriately wide audience!  The two adverbs of choice for the double-dactyl structure attempted to highlight this, via the combination of “quietly” and “mightily.”  

“Physical, chemical /
Thermodynamical /
Tools: spontaneity 
Can be explored.”
Gibbs’s work was fundamental to the field of chemical thermodynamics, and several equations and concepts bear his name.  The most famous of these is likely the Gibbs Free Energy, represented with a capital G.  The Gibbs Free Energy is a state function, and the change in this quantity for a given chemical reaction can be quantified (Delta G, or 𝛥G), by taking the free energy of the products minus the free energy of the reactants.  If 𝛥G has a negative sign, it means the reaction will proceed spontaneously (naturally).  

This is a particularly useful quantity for chemists because it defines spontaneity at constant temperature and pressure.  Moreover, it allows chemists to discern whether a process will be spontaneous by considering the system (reaction) alone; this is often more convenient than directly using the Second Law of Thermodynamics, which also defines spontaneity but requires consideration of both a system and its surroundings to do so.     

Categories
Science Poetry

In the Cards

“Patiently, spatially, /
D. Mendeleev /
Arranges the elements by column and row. / 
Prescriptive, predictive, /
The table finds favor /
In ‘eur-eka’ moments with space apropos.” 

The 8 July 2019 poem was inspired by a call from Chemical and Engineering News for entries to a Periodic Poetry contest in mid-July.  This poem is a different form of light verse than the limericks that began this project; it is likely best characterized as a modification of the “higgledy piggledy,” or “double dactyl.”  It does not adhere particularly well to the actual rules for that poem format, which are quite specific and numerous.  However, the use of a proper name in line two, its theme regarding a historic event, and the metric feet employed are all aspects that align most closely with the double dactyl form.  

“Patiently, spatially, / D. Mendeleev /
Arranges the elements by column and row.” 
In 1869, Dmitri Mendeleev devised the first form of what we recognize today as the modern Periodic Table of the Elements (PTE).  In 2019, several events marked the 150th anniversary of that innovation.  According to some sources, Mendeleev was a card player who particularly enjoyed the game Patience, similar to Solitaire, in which cards are spatially arranged according to both suit and number.  This provided partial inspiration for his innovation regarding the periodic table’s structure: in the modern PTE, the 118 known elements are arranged according to both atomic numbers (rows) and characteristic properties (columns).        

“Prescriptive, predictive, / The table finds favor / 
In ‘eur-eka’ moments with space apropos.” 
Mendeleev took advantage of known chemical data in creating his PTE precursor, fitting elements into a pattern that placed elements into chemical families with similar properties and reactivities; he also left gaps where there wasn’t an obvious candidate to fit in a space.  The table was thus prescriptive, summarizing known information, and predictive, forecasting the properties and reactivities of newly discovered elements that would fill in the gaps.  

Mendeleev named these yet-to-be-discovered elements according to their chemical relatives.  For instance, he left a gap for an element he deemed “eka-aluminum,” with an expected placement one spot below aluminum (the Sanskrit prefix for “one” is “eka”), expecting that an element with certain properties and reactivities would be discovered and would fit there.  When gallium was isolated in 1875, its properties matched Mendeleev’s predictions for eka-aluminum (and, further, provided a “eureka” moment of scientific discovery!).  This and other “space[s] apropos” played a major role in chemists’ adoption of the periodic table. 

Categories
April 2019 Limerick Project

Kekulé and Benzene

“The structure of resonant benzene
Found inception in Kekule’s daydream
As a snake seized its tail:
Vivid image availed
Him an insight once shrouded in smokescreen.”

The 14 April 2019 limerick retells a famous legend from chemical history: German organic chemist August Kekulé’s 1865 inspiration regarding the shape of the molecule benzene.

A major theme of chemistry is that the shapes (the structures) of molecules impact their behaviors (their functions); analyses of these structure-function relationships are part of many fields of chemistry research. With many compounds, their behaviors were observed in the laboratory before their chemical structures were known, and the paths to understand those structures include many interesting stories.

This story also provides a convenient overview of three types of chemical representations: empirical, molecular, and structural formulas.

“The structure of resonant benzene/
Found inception in Kekule’s daydream/
As a snake seized its tail…”
The molecule benzene contains six carbon atoms and six hydrogen atoms, as described by its molecular formula: C6H6. Before scientists understood this, they knew benzene’s empirical formula, which represents the lowest possible ratio of elements: here, CH. Since all that was known was that the molecule contained one carbon atom for every hydrogen atom, many possibilities were imagined for its shape.

According to legend, Kekulé had been pondering this question, when he had a daydream about a snake biting its tail. This inspired his idea of a cyclic compound, one in which carbon atoms formed a ring, instead of connecting to one another in a linear chain.

We now represent benzene as existing in a hexagonal shape, as succinctly shown via its structural formula. After Kekulé’s revelation, further study of benzene revealed an interesting bonding pattern called resonance, which accounts for benzene’s unusual stability.

“Vivid image availed/
Him an insight once shrouded in smokescreen.”
Kekulé later popularized the dramatic nature of his insight, writing: “One of the snakes had seized hold of its own tail, and the form whirled mockingly before my eyes. As if by a flash of lightning I awoke… I spent the rest of the night in working out the consequences of the hypothesis.”

As with many of the stories behind scientific discoveries, debates have arisen as to the veracity of the details. That said, the last line of this limerick is a final allusion to the chemical legend, since it is generally recounted that Kekulé had his daydream in front of the fireplace.