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Title: Directed Gas-Phase Synthesis of Triafulvene under Single-Collision Conditions

Journal Article · · Angewandte Chemie (International Edition)
ORCiD logo [1];  [1];  [1];  [2]; ORCiD logo [3]; ORCiD logo [1]
  1. Univ. of Hawaii at Manoa, Honolulu, HI (United States)
  2. Samara National Research Univ., Samara (Russian Federation); Florida International Univ., Miami, FL (United States)
  3. Florida International Univ., Miami, FL (United States)
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We report the triafulvene molecule (c-C4H4)—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 (CH3CCH) and allene (H2CCCH2) 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 C3H4 isomer followed by unimolecular decomposition through elimination of atomic hydrogen from the CH3 or CH2 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).

Research Organization:
Univ. of Hawaii at Manoa, Honolulu, HI (United States); Florida International Univ. (FIU), Miami, FL (United States); Univ. of Hawaii, Honolulu, HI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
FG02-03ER15411; FG02-04ER15570
OSTI ID:
1603226
Alternate ID(s):
OSTI ID: 1560246; OSTI ID: 1594728
Journal Information:
Angewandte Chemie (International Edition), Vol. 58, Issue 43; ISSN 1433-7851
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

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Figures / Tables (17)

Scheme 1(p. 3)figure Scheme 1
Scheme 2(p. 4)figure Scheme 2
Scheme 3(p. 4)figure Scheme 3
Figure 1(p. 6)figure Figure 1
Figure 2(p. 8)figure Figure 2
Figure 3(p. 10)figure Figure 3
Figure 4(p. 11)figure Figure 4
Figure 5(p. 13)figure Figure 5
Table S1(p. 20)table Table S1
Table S2(p. 21)table Table S2
Figure S1(p. 22)figure Figure S1
Figure S2(p. 23)figure Figure S2
Figure S3(p. 24)figure Figure S3
Figure S4(p. 25)figure Figure S4
Figure S5(p. 26)figure Figure S5
Figure S6(p. 27)figure Figure S6
Figure S7(p. 28)figure Figure S7

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
gas-phase reactions
radicals
reaction dynamics
strained molecules
triafulvene