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Originally published in Science Express on 13 April 2006
Science 5 May 2006:
Vol. 312. no. 5774, pp. 722 - 724
DOI: 10.1126/science.1126675
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Reports

Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory

Vincent Lavallo,1 Yves Canac,1 Bruno Donnadieu,1 Wolfgang W. Schoeller,2 Guy Bertrand1*

Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C3H2) has been presumed to be too unstable to isolate in the laboratory. However, by appending {pi}-electron–donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium.

1 University of California, Riverside–CNRS Joint Research Chemistry Laboratory (Unité Mixte Internationale 2957), Department of Chemistry, University of California, Riverside, CA 92521–0403, USA.
2 Fakultät für Chemie der Universität, Postfach 10 01 31, D-33615 Bielefeld, Germany.

* To whom correspondence should be addressed. E-mail: gbertran{at}mail.ucr.edu

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