Premium
Directed Gas‐Phase Synthesis of Triafulvene under Single‐Collision Conditions
Author(s) -
Thomas Aaron M.,
Zhao Long,
He Chao,
Galimova Galiya R.,
Mebel Alexander M.,
Kaiser Ralf I.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908039
Subject(s) - chemistry , allene , cycloaddition , fulvene , molecule , photochemistry , gas phase , computational chemistry , hydrogen , hydrocarbon , dipole , organic chemistry , catalysis
The triafulvene molecule (c‐C 4 H 4 )—the simplest representative of the fulvene family—has been synthesized for the first time in the gas phase through the reaction of the methylidyne radical (CH) with methylacetylene (CH 3 CCH) and allene (H 2 CCCH 2 ) under single‐collision conditions. The experimental and computational data suggest triafulvene is formed by the barrierless cycloaddition of the methylidyne radical to the π‐electron density of either C 3 H 4 isomer followed by unimolecular decomposition through elimination of atomic hydrogen from the CH 3 or CH 2 groups of the reactants. The dipole moment of triafulvene of 1.90 D suggests that this molecule could represent a critical tracer of microwave‐inactive allene in cold molecular clouds, thus defining constraints on the largely elusive hydrocarbon chemistry in low‐temperature interstellar environments, such as that of the Taurus Molecular Cloud 1 (TMC‐1).