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Chemists Make Urea With A P

Oxford researchers synthesize a phosphorus analog of urea, nearly 200 years after Wöhler’s synthesis help put synthetic organic chemistry on the map

by Stephen K. Ritter
December 23, 2013 | A version of this story appeared in Volume 91, Issue 51

Friedrich Wöhler made chemical history in 1828 when he became the first person to synthesize an organic compound from inorganic starting materials—he serendipitously prepared urea, H2NC(O)NH2, from silver cyanate and ammonium chloride. That milestone is considered by some historians as the birth of modern organic chemistry. Nearly 200 years later, Wöhler’s synthesis has inspired a pair of Oxford University chemists to explore similarities between cyanate, N≡C–O, and its heavier analog phosphaethynolate, P≡C–O, leading them to the first synthesis of a phosphorus analog of urea, H2PC(O)NH2 (J. Am. Chem. Soc. 2013, DOI: 10.1021/ja4115693). Andrew R. Jupp and Jose M. Goicoechea prepared the phosphorus version, which is a stable liquid at room temperature, by treating a phosphaethynolate potassium crown ether complex with an ammonium salt. Before Wöhler’s time, urea was already known to be a by-product of human metabolism and as such the main nitrogen-containing compound in urine. Urea today is used industrially as a nitrogen source in fertilizer and as a starting material to make plastics and adhesives. Jupp and Goicoechea believe the phosphorus analog could play a similar role to make phosphorus-containing plastics and could serve as a ligand in coordination compounds.


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