Analytical Study of Superaromaticity in Cycloarenes and Related Coronoid Hydrocarbons

被引：58

作者：

Aihara, Jun-ichi ^{[1
,2
]}

Makino, Masakazu ^{[2
]}

Ishida, Toshimasa ^{[3
]}

Dias, Jerry R. ^{[4
]}

机构：

[1] Shizuoka Univ, Dept Chem, Fac Sci, Shizuoka 4228529, Japan

[2] Univ Shizuoka, Inst Environm Sci, Shizuoka 4228526, Japan

[3] Kyoto Univ, Fukui Inst Fundamental Chem, Kyoto 6068103, Japan

[4] Univ Missouri, Dept Chem, Kansas City, MO 64110 USA

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2013年 / 117卷 / 22期

关键词：

POLYCYCLIC AROMATIC-HYDROCARBONS; HEXAGONAL GRAPHENE NANOFLAKES; INDEPENDENT CHEMICAL-SHIFTS; CIRCUIT RESONANCE ENERGY; SUPER-RING MOLECULE; BENZENOID HYDROCARBONS; CONJUGATED HYDROCARBONS; MACROCYCLIC AROMATICITY; ELECTRONIC-PROPERTIES; MAGNETIC-RESONANCE;

D O I：

10.1021/jp4016678

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：

Recently synthesized septulene is a unique cycloarene molecule in that no macrocyclic conjugation circuits can be chosen from the pi-system. This molecule has essentially no superaromatic stabilization energy (SSE) and can be viewed as an ideal nonsuperaromatic macrocyde. SSEs for kekulene and other cycloarenes are also very small. In these hydrocarbons, a macrocyde formed by fused benzene rings effectively suppresses not only the aromaticity inherent in macrocyclic (4n+2)-site conjugation circuits but also the antiaromaticity inherent in macrocyclic (4n +/- 1)-site circuits. Comparative study of superaromaticity in multilayered coronoid hydrocarbons revealed that not only SSE but also the HOMO contribution to SSE is minimized in odd-layered coronoids.

引用

页码：4688 / 4697

页数：10

共 71 条

[1] BOND RESONANCE ENERGY AND VERIFICATION OF THE ISOLATED PENTAGON RULE [J].

AIHARA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (14) :4130-4136

[2] NON-SUPERAROMATIC REFERENCE DEFINED BY GRAPH-THEORY FOR A SUPER-RING MOLECULE [J].

AIHARA, J .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1995, 91 (02) :237-239

[3] NUMBER OF AROMATIC SEXTETS IN A BENZENOID HYDROCARBON [J].

AIHARA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (05) :1429-1430

[4] Huckel-like rule of superaromaticity for charged paracyclophanes [J].

Aihara, J .

CHEMICAL PHYSICS LETTERS, 2003, 381 (1-2) :147-153

[5] GRAPH-THEORETICAL FORMULA FOR RING CURRENTS INDUCED IN A POLYCYCLIC CONJUGATED SYSTEM [J].

AIHARA, J ;

HORIKAWA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (06) :1853-1854

[6] GRAPH-THEORETICAL FORMULATION OF LONDON DIAMAGNETISM [J].

AIHARA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) :5913-5917

[7] Non-superaromatic reference for carbon nanotube as a quasi-one-dimensional pi-bonding model for graphite [J].

Aihara, J ;

Tamaribuchi, T .

JOURNAL OF MATHEMATICAL CHEMISTRY, 1996, 19 (3-4) :231-239

[8] GENERAL FORMULAS FOR EVALUATING RING CURRENTS INDUCED IN A POLYCYCLIC CONJUGATED SYSTEM [J].

AIHARA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (03) :1045-1046

[9] MAGNETOTROPISM OF BIPHENYLENE AND RELATED HYDROCARBONS - A CIRCUIT CURRENT ANALYSIS [J].

AIHARA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :298-302

[10] NEW DEFINITION OF DEWAR-TYPE RESONANCE ENERGIES [J].

AIHARA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2750-2758

← 1 2 3 4 5 6 7 8 →