Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Determination of Atomic Structures and Relative Stabilities of Diadduct Regioisomers of C20X2 (X = H, F, Cl, Br, and OH) by the Hybrid Density-Functional B3LYP Method

  • Lee, Seol (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University) ;
  • Suh, Young-Sun (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University) ;
  • Hwang, Yong-Gyoo (Division of Microelectronics and Display Technology, and Nanoscale Sciences and Technology Institute, Wonkwang University) ;
  • Lee, Kee-Hag (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University)
  • Received : 2011.06.09
  • Accepted : 2011.07.27
  • Published : 2011.09.20
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Abstract

We have studied the relative stability and atomic structures of five $C_{20}X_2$ regioisomers obtained as diadducts of a $C_{20}$ cage (X = H, F, Cl, Br, and OH). All the regioisomers are geometric isomers, i.e., they differ in their spatial arrangement. Full-geometry optimizations of the regioisomers have been performed using the hybrid density-functional (B3LYP/6-31G(d, p)) method. Our results suggest that the cis-1 regioisomer (the 1,2-diadduct) is the most stable and that the second most stable is the trans-2 (1,13-diadduct) regioisomer, implying that the long-range interaction between the two adducts and the resonance effect are more pronounced than the diadduct-induced strain in the $C_{20}$ cage. The HOMO and LUMO characteristics of each regioisomer with the same symmetry of structural regioisomers except $C_{20}(OH)_2$ are topologically same. This suggests that by using an entirely different set of characteristic chemical reactions for each regioisomer, we can distinguish between the five regioisomers for each $C_{20}$ diadduct derivative.

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