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Published Online April 13, 2006
Science DOI: 10.1126/science.1126675

Reports

Submitted on February 24, 2006
Accepted on March 31, 2006

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 Bertrand 1*

1 UCR-CNRS Joint Research Chemistry Laboratory (UMI 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.
Guy Bertrand , E-mail: gbertran{at}mail.ucr.edu

Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C3H2), has been presumed too unstable to isolate in the laboratory. However, by appending {pi}-electron donating amino groups to the triangular skeleton, we have 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.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Stable four-{pi}-electron, four-membered heterocyclic cations and carbenes.
Y. Ishida, B. Donnadieu, and G. Bertrand (2006)
PNAS 103, 13585-13588
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Science. ISSN 0036-8075 (print), 1095-9203 (online)