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Research Team Synthesizes a New Class of Stable Organic Compounds

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Patrick Antoni and Max Hansmann (from left). © TU Dort­mund
Doctoral candidate Patrick Antoni (l.) and JProf. Max Martin Hansmann (r.) re­cent­ly published their findings in the re­nowned scientific journal Nature Chem­is­try.

Scientists at TU Dort­mund Uni­ver­sity have achieved an im­por­tant advance in organic chem­is­try: They have managed to isolate and characterize a new highly reactive organic compound at room temperature. Their findings were re­cent­ly published in the re­nowned scientific journal Nature Chem­is­try.

In organic chem­is­try, sci­en­tists synthesize new organic mol­ecules and characterize their chemical and physicochemical properties. The material properties and reaction behavior are essentially determined by functional groups, which can consist of different elements: carbon (C), hydrogen (H), nitrogen (N), oxygen (O), sulfur (S), phosphorus (P), and halogens. One example is the hydroxyl group (-OH) of the alcohols. For most of the functional groups, synthesis and reactivity have already been thoroughly investigated. But there are also functional groups that are so reactive that the compounds cannot be isolated at room temperature. Previously, one such highly reactive molecule class was the class of diazoalkenes (R2C=C=N=N). Because of their high reactivity, they are very difficult to synthesize and typically are only “stable” at temperatures of a few Kelvin. Therefore they had been characterized in organic chem­is­try only at very low temperatures, until now.

By taking advantage of an unusual synthesis route and an electronic trick, the re­search group led by JProf. Max Hansmann at TU Dort­mund Uni­ver­sity has now managed to isolate and characterize the first compound with such a functional group at room temperature. To do this, they activated laughing gas (N2O), a molecule that is normally very difficult to activate, and transferred the nitrogen it contains to a special compound, an ylidic polarized olefin. “It is amazing that such a functional group based on carbon and nitrogen, two elements so central to organic chem­is­try, had not been synthesized before,” says JProf. Hansmann. “The first-ever successful production of this molecule that is stable at room temperature opens up numerous interesting reactions, which bring with them in turn a wide range of possible applications.” In the fu­ture, for instance, the results of this proj­ect in fundamental science could potentially have an impact on the development of new drugs or materials.

JProf. Hansmann’s team collaborated with other partners on this proj­ect: To unambiguously verify the molecular structure of the diazoalkene using X-ray diffraction, Hansmann’s team was supported by Dr. Christopher Golz from the Uni­ver­sity of Göttingen and Dr. Julian Holstein of TU Dort­mund Uni­ver­sity. In addition, Dr. Dimitrios Pantazis from the Max Planck In­sti­tute for Coal Research in Mülheim contributed by using quantum chemical methods to conduct a more detailed analysis of the electronic structure.

Original publication in Nature Chem­is­try

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