Montana State University

MSU chemists solve long-standing problem, explain in international journal

December 22, 2014 -- By Evelyn Boswell, MSU News Service

This MSU image was featured in the Dec. 22 issue of the scientific journal Angewandte Chemie. It shows how the carbon-nitrogen bond is formed with the help of the zinc-based metal.

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BOZEMAN – A Montana State University team says it has discovered the grail of organic chemistry and has just published a paper about its accomplishment in one of the field’s top journals.

The paper by professor Tom Livinghouse and graduate students Bryce Sunsdahl and Adrian Smith appears in the Dec. 22 issue of the German chemistry journal Angewandte Chemie.

First published online in October, the highly technical paper explains how the team in MSU’s Department of Chemistry and Biochemistry developed an inexpensive and environmentally friendly way to sequentially produce carbon-nitrogen and carbon-carbon bonds commonly found in antibiotics and other pharmaceuticals for humans and animals.

Organic chemists often produce a mixture of unneeded products in the process of making the one they want, Livinghouse explained. As a result, they often throw much material away and keep the one they want.

To solve that long-standing problem, Livinghouse said the MSU group developed a one-step process that largely eliminates waste products. The process is extremely efficient, and it saves time and money. Livinghouse describes it as green chemistry because the process is non-toxic and produces few byproducts. If done right, it minimizes the needs for external solvents. Scientists get “two bonds for the price of one.”

The MSU team isn’t the first to come up with the idea, but the techniques developed by other groups over the past 15 years have had very limited application, Livinghouse said.

“What we did can apply to a great many pharmaceuticals,” he said.

Livinghouse said he came up with the idea about three years ago, but he praised his graduate students for making it happen over the past year. He said their work in the lab was critical to the success of the project and the newly published paper.

“Only with the very best graduate students can you do this,” Livinghouse said. “I’m very proud of my students.

“I couldn’t have done it without them,” he added. “That’s what science is all about. That’s what the university is all about.”

The paper was Sunsdahl’s first published paper. When he learned it had been accepted for publication, Sunsdahl said, “I celebrated by doing more chemistry.”

Sunsdahl, who is listed as first author of the paper, said his main role in the breakthrough described in Angewandte Chemie was developing and streamlining the methodology for the new chemical reaction.

Sunsdahl is pursuing doctoral degree in organic chemistry and plans to graduate in the spring. With his family in St. Cloud, Minn., and only seeing them every few weeks, he said he often works late into the night in Livinghouse’s laboratory.

Smith from Escanaba, Mich., is working on his doctorate in organic chemistry and also plans to graduate in the spring.

“This is my third publication, but definitely the most prestigious one I have been a part of,” Smith said.

Livinghouse has been published once before in Angewandte Chemie, but he said the potential impact of his latest paper is much more significant than the first. In fact, he submitted his paper to the German journal because it is the most select journal in the field of organic chemistry. After learning the paper had been accepted for publication, Livinghouse said he was pleased by the recognition.

“We have been doing great chemistry in my group and throughout the department for a great many years,” he said.

By Evelyn Boswell, MSU News Service