Theoretical Study on the Reaction Mechanism of Azacyclopropenylidene with Epoxypropane: An Insertion Process 


Vol. 35,  No. 9, pp. 2717-2722, Sep.  2014
10.5012/bkcs.2014.35.9.2717


PDF
  Tumbnail

  Abstract

The reaction mechanism between azacyclopropenylidene and epoxypropane has been systematically investigated employing the second-order Møller-Plesset perturbation theory (MP2) method to better understand the reactivity of azacyclopropenylidene with four-membered ring compound epoxypropane. Geometry optimization, vibrational analysis, and energy property for the involved stationary points on the potential energy surface have been calculated. It was found that for the first step of this reaction, azacyclopropenylidene can insert into epoxypropane at its C-O or C-C bond to form spiro intermediate IM. It is easier for the azacyclopropenylidene to insert into the C-O bond than the C-C bond. Through the ring-opened step at the C-C bond of azacyclopropenylidene fragment, IM can transfer to product P1, which is named as pathway (1). On the other hand, through the H-transferred step and subsequent ring-opened step at the C-N bond of azacyclopropenylidene fragment, IM can convert to product P2, which is named as pathway (2). From the thermodynamics viewpoint, the P2 characterized by an allene is the dominating product. From the kinetic viewpoint, the pathway (1) of formation to P1 is primary.

  Statistics
Cumulative Counts from November, 2022
Multiple requests among the same browser session are counted as one view. If you mouse over a chart, the values of data points will be shown.


  Cite this article

[IEEE Style]

X. Tan, W. Wang, P. Li, "Theoretical Study on the Reaction Mechanism of Azacyclopropenylidene with Epoxypropane: An Insertion Process," Bulletin of the Korean Chemical Society, vol. 35, no. 9, pp. 2717-2722, 2014. DOI: 10.5012/bkcs.2014.35.9.2717.

[ACM Style]

Xiaojun Tan, Weihua Wang, and Ping Li. 2014. Theoretical Study on the Reaction Mechanism of Azacyclopropenylidene with Epoxypropane: An Insertion Process. Bulletin of the Korean Chemical Society, 35, 9, (2014), 2717-2722. DOI: 10.5012/bkcs.2014.35.9.2717.

Search
(IN TITLE, AUTHOR, ABSTRACT,KEYWORDS)

Advanced Search ▼

POPULAR KEYWORDS
(TOP 10 KEYWORDS)

Recent Publications
(LAST 3 YEARS)

ISSN(Print) 0253-2964
ISSN(Online) 1229-5949