Chemistry for Everyone
Fifty Ways To Make Boric Acid (with Apologies to Paul Simon) Craig M. Davis Department of Chemistry, Xavier University, Cincinnati, OH 45207-4221;
[email protected] As a graduate student at Syracuse University I worked with boranes (boron and hydrogen clusters) and their metal derivatives. All too often the intermediates or products decomposed to boric acid. I constantly lamented to another group member (John Glass) that I could write a song about “fifty ways to make boric acid”, an obvious parody of the Paul Simon song “Fifty Ways to Leave Your Lover”. One night after group meeting John told me to stop saying I could write the song, and actually write it. Much to my surprise, I finished the lyrics in about one hour. The suggestion to “switch to carboranes” reflects my experience as a post-doc at the University of Virginia; our metal derivatives of carboranes (carbon, boron, and hydrogen clusters) were so stable that we could run them down silica-gel columns sitting on a benchtop. The reference to photochemistry is a tribute to the technique that led to my first publication as a graduate student. “Your problems all lie in your solvents,” she said to me. “The answer is easy, if you degas them thoroughly.” I learned what every boron chemist learns so painfully: There must be . . . fifty ways to make boric acid. Organic-synthesis friends tell me with such glee, “I’ve reached my fifteenth step with ninety-percent ‘ee’.” Then they chuckle when I respond so humbly that, “I’ve found . . . fifty ways to make boric acid.” Just leak a little air, Blair. Fill a flask that’s wet, Chet. Or, let it get warm, Norm. Now, listen to me. Using silica gel, Mel, sounds your product’s death knell. So switch to carboranes, Jane, and set yourself free. Boron hydrides are not child’s play, so I went to speak to my advisor yesterday. I told him, “If you have any secrets, I will gladly pay to hear about those fifty ways . . .” He said, “Stirring reagents in a flask is just too slow. It appears that photochemistry is the way to go. But, be careful your whole system doesn’t blow, or you’ll learn . . . fifty ways to mop boric acid.” Just leak a little air, Blair. Fill a flask that’s wet, Chet. Or, let it get warm, Norm. Now, listen to me. Using silica gel, Mel, sounds your product’s death knell. So switch to carboranes, Jane, and set yourself free.
www.JCE.DivCHED.org
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Vol. 82 No. 4 April 2005
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Journal of Chemical Education
541
