Synthesis and Characterization of Cyanobutadiene Isomers-Molecules of Astrochemical Significance

Samuel M. Kougias, Stephanie N. Knezz, Andrew N. Owen, Rodrigo A. Sanchez, Grace E. Hyland, Daniel J. Lee, Aatmik R. Patel, Brian J. Esselman, R. Claude Woods, Robert J. McMahon

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Four cyanobutadiene isomers of considerable interest to the organic chemistry, molecular spectroscopy, and astrochemistry communities were synthesized in good yields and isolated as pure compounds: (E)-1-cyano-1,3-butadiene (E-1), (Z)-1-cyano-1,3-butadiene (Z-1), 4-cyano-1,2-butadiene (2), and 2-cyano-1,3-butadiene (3). A diastereoselective synthesis was developed to generate (E)-1-cyano-1,3-butadiene (1) (10:1 E/Z) via tandem SN2 and E2′ reactions. The potential energy surfaces of the E2′ reactions leading to (E)- A nd (Z)-1-cyano-1,3-butadiene (1) were analyzed by density functional theory calculations, and the observed diastereoselectivity was rationalized in the context of the Curtin-Hammett principle. The preparation of pure samples of these reactive compounds enables measurement of their laboratory rotational spectra, which are the critical data needed to search for these species in space by radioastronomy.

Original languageEnglish (US)
Pages (from-to)5787-5798
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number9
DOIs
StatePublished - May 1 2020
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and Characterization of Cyanobutadiene Isomers-Molecules of Astrochemical Significance'. Together they form a unique fingerprint.

Cite this