Theoretical study on the mechanism of the addition reaction between cyclopropenylidene and formaldehyde

Tan, Xiaojun, Li, Zhen, Sun, Qiao, Li, Ping and Wang, Weihua (2012) Theoretical study on the mechanism of the addition reaction between cyclopropenylidene and formaldehyde. Bulletin of the Korean Chemical Society, 33 6: 1934-1938. doi:10.5012/bkcs.2012.33.6.1934


Author Tan, Xiaojun
Li, Zhen
Sun, Qiao
Li, Ping
Wang, Weihua
Title Theoretical study on the mechanism of the addition reaction between cyclopropenylidene and formaldehyde
Journal name Bulletin of the Korean Chemical Society   Check publisher's open access policy
ISSN 0253-2964
1229-5949
Publication date 2012-06-01
Sub-type Article (original research)
DOI 10.5012/bkcs.2012.33.6.1934
Open Access Status DOI
Volume 33
Issue 6
Start page 1934
End page 1938
Total pages 5
Place of publication Seoul, Republic of Korea
Publisher Korean Chemical Society
Collection year 2013
Language eng
Formatted abstract
The reaction mechanism between cyclopropenylidene and formaldehyde has been systematically investigated
employing the MP2/6-311+G* level of theory to better understand the cyclopropenylidene reactivity with
carbonyl compound. Geometry optimization, vibrational analysis, and energy property for the involved
stationary points on the potential energy surface have been calculated. Energies of all the species are further
corrected by the CCSD(T)/6-311+G* single-point calculations. It was found that one important reaction
intermediate (INTa) has been located firstly via a transition state (TSa). After that, the common intermediate
(INTb) for the two pathways (1) and (2) has been formed via TSb. At last, two different products possessing
three- and four-membered ring characters have been obtained through two possible reaction pathways. In the
reaction pathway (1), a three-membered ring alkyne compound has been obtained. As for the reaction pathway
(2), it is the formation of the four-membered ring conjugated diene compound. The energy barrier of the ratedetermining
step of pathway (1) is lower than that of the pathway (2), and the ultima product of pathway (2) is
more stable than that of the pathway (1).
Keyword Cyclopropenylidene
Formaldehyde
Addition reaction
Theoretical study
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Australian Institute for Bioengineering and Nanotechnology Publications
 
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