Some reactions and properties of molecular C sub 2. An experimental and theoretical treatment

Journal Article · Wed Jun 07 04:00:00 EDT 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00194a042· OSTI ID:7073231

Skell, P S; Jackman, L M; Ahmed, S ^[1]; McKee, M L; Shevlin, P B ^[2]

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1. Pennsylvania State Univ., University Park (USA)
2. Auburn Univ., AL (USA)

Diatomic carbon, C{sub 2}, reacts with propylene and (E)- and (Z)-2-butene in the condensed phase at 77 K. Products can be rationalized by a mechanism involving initial addition of C{sub 2} to the alkene to generate a 1,4-diradical. This diradical may then either abstract hydrogens or add another alkene molecule to give a 1,6-diradical which disproportionates to an enyne. Thus, reaction of C{sub 2} with propene gives 1-pentyne, 3-methyl-l-butyne, 4-methylhept-6-en-1-yne, 6-methylhept-1-en-4-yne, and oct-1-en-4-yne. Ab initio calculations at the HF/3-21G level predict that both {sup 1}C{sub 2} and {sup 3}C{sub 2} will add to ethylene without barrier. At the MP2/6-31G*//3-21G level, the triplet adduct is calculated to be more stable than {sup 3}C{sub 2} and ethylene by 46.0 kcal/mol. The reactions of {sup 1}C{sub 2} and {sup 3}C{sub 2} with methane and hydrogen have also been investigated theoretically.

• OSTI ID: 7073231
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:12; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
360603* -- Materials-- Properties
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400000 -- Chemistry
400201 -- Chemical & Physicochemical Properties
ALGAE
ALKENES
CALCULATION METHODS
CARBON
CHEMICAL REACTIONS
CHROMOPHYCOTA
DATA
DIATOMS
ELEMENTS
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
LOW TEMPERATURE
MEASURING INSTRUMENTS
MEASURING METHODS
MOLECULAR STRUCTURE
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
PLANTS
PROPYLENE
THEORETICAL DATA