On the aromatic stabilization of corannulene and coronene

被引：30

作者：

Dobrowolski, Michal A. ^{[1
]}

Ciesielski, Arkadiusz ^{[1
,2
]}

Cyranski, Michal K. ^{[1
]}

机构：

[1] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland

[2] Polish Acad Sci, Inst Biochem & Biophys, PL-02106 Warsaw, Poland

来源：

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | 2011年 / 13卷 / 46期

关键词：

MOLECULAR-ORBITAL CALCULATIONS; INDEPENDENT CHEMICAL-SHIFTS; PI-ELECTRON DELOCALIZATION; RING CURRENTS; GEODESIC POLYARENES; ORGANIC-COMPOUNDS; HYDROCARBONS; ENERGIES; DERIVATIVES; FULLERENES;

D O I：

10.1039/c1cp21994d

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The application of set of homodesmotic reactions allowed us to estimate the aromatic stabilization energy (ASE) of corannulene and coronene. Appropriate reactions have been applied to balance syn/anti mismatches in di-, tetra- and hexamethylene substituted derivatives. Based on many different polycyclic reference structures that compensate the effect of strain in the corannulene moiety the value of ASE comes to 44.5 kcal mol(-1). Planar corannulene is more stabilized by cyclic p-electron delocalization by ca. 10.7 kcal mol(-1), as compared with a bowl-shaped system. A similar approach for coronene leads to an ASE equal to 58.4 kcal mol(-1).

引用

页码：20557 / 20563

页数：7

共 50 条

[1]

BARTH WE, 1971, J AM CHEM SOC, V93, P1730

[2] DIBENZO[GHI,MNO]FLUORANTHENE [J].