Kendall N. Houk holds UCLAs Saul Winstein Chair in Organic Chemistry. (Credit: Reed Hutchinson/UCLA)
(Phys.org) -- In 1928, chemists Otto Diels and Kurt Alder first documented diene synthesis, a chemical reaction important for synthesizing many polymers, alkaloids and steroids. Their work on this mechanism, which came to be known as the DielsAlder reaction, won them the 1950 Nobel Prize in chemistry.
Since then, the iconic reaction has become the most commonly used and studied mechanism in organic chemistry. But what happens during the reaction has never been entirely clear.
Now, Kendall N. Houk, UCLA's Saul Winstein Professor of Organic Chemistry, and colleagues report exactly how the DielsAlder reaction occurs. Their research is published this week in the early online edition of the journal Proceedings of the National Academy of Sciences and will be published in an upcoming print edition.
"We have examined the molecular dynamics of the DielsAlder reaction, which has become the most important reaction in synthesis, in detail to understand how it happens," said Houk, who is a member of the California NanoSystems Institute at UCLA.
Houk and his colleagues created a number of simulations he calls them short movies of molecules coming together and reacting.
One of Houk's DielsAlder movies:
(Houk isn't the only one making movies about DielsAlder. UCLA organic chemistry students in Professor Neil Garg's class have produced a series of amusing music videos in which they reference the reaction: Watch "Chemistry Jock" [reference at 2:08], "Hey There Neil Garg" [1:44] and "Payphone" [1:07].)
"The idea," Houk said, "is to understand how the reaction happens not just that A goes to B and B goes to C, but to actually follow how the bonds are forming and how the atoms are moving as these things come together. Using the massive computing power we have now, we get a degree of resolution of the mechanism that was not really possible before. It took a lot of computer time, but as a result, we now have unprecedented insight into how this reaction occurs."
Organic chemists have argued about this for years: If two bonds form during a reaction, do they form at the same time, or does one form first and then the other?
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New insights into how the most iconic reaction in organic chemistry really works
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