DELOCALIZATION ENERGY OF PI ELECTRONS AS AN INDEX FOR AROMATICITY OF POLYCYCLIC-HYDROCARBONS

被引：44

作者：

BEHRENS, S ^{[1
]}

KOSTER, AM ^{[1
]}

JUG, K ^{[1
]}

机构：

[1] UNIV HANNOVER, D-30167 HANNOVER, GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 09期

关键词：

D O I：

10.1021/jo00088a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SINDO1 calculations of an improved pi electron delocalization energy with geometry optimization were performed for a large number of mono- and polycyclic hydrocarbon rings and compared with ab initio results. The suitability of the delocalization energy as aromaticity index is demonstrated. For a comparison of the aromaticity of molecules with different size and different number of rings, a normalized delocalization energy per broken pi bond in the reference state was introduced. With this criterion the aromaticity of polycyclic conjugated hydrocarbons with four- and six-membered rings was examined and an energetic aromaticity scale established.

引用

收藏

页码：2546 / 2551

页数：6

相关论文

共 43 条

[1] EFFECT OF BOND-LENGTH ALTERNATION ON THE AROMATICITY OF BENZENE [J].

AIHARA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) :1956-1960

[2]

ALLINGER NL, 1980, ORGANISCHE CHEM, P397

[3] ON THE DRIVING FORCE FOR THE SYMMETRICAL STRUCTURE OF BENZENE AND THE ALLYL RADICAL - SIGMA OR PI [J].

BAIRD, NC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3907-3908

[4] BOND ALTERNATION IN TRIANNELATED BENZENES - DISSECTION OF CYCLIC PI FROM MILLS NIXON EFFECTS [J].

BALDRIDGE, KK ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9583-9587

[5] POLYCYCLIC BIPHENYLENES .5. THE PMR SPECTRA OF ANNELATED BIPHENYLENES [J].

BARTON, JW ;

ROWE, DJ .

TETRAHEDRON, 1985, 41 (07) :1323-1328

[6] A NEW APPROACH TO THE CONSTRUCTION OF BIPHENYLENES BY THE COBALT-CATALYZED COCYCLIZATION OF ORTHO-DIETHYNYLBENZENES WITH ALKYNES - APPLICATION TO AN ITERATIVE APPROACH TO [3]PHENYLENE, THE 1ST MEMBER OF A NOVEL CLASS OF BENZOCYCLOBUTADIENOID HYDROCARBONS [J].

BERRIS, BC ;

HOVAKEEMIAN, GH ;

LAI, YH ;

MESTDAGH, H ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5670-5687

[7] CONSTRUCTION OF SOME MOLECULAR ORBITALS TO BE APPROXIMATELY INVARIANT FOR CHANGES FROM ONE MOLECULE TO ANOTHER [J].

BOYS, SF .

REVIEWS OF MODERN PHYSICS, 1960, 32 (02) :296-299

[8]

DEWAR MJS, 1989, HETEROCYCLES, V28, P1135

[9]

Dewar MJS., 1969, MOL ORBITAL THEORY O

[10] TRIS(BENZOCYCLOBUTADIENO)BENZENE, THE TRIANGULAR [4]PHENYLENE WITH A COMPLETELY BOND-FIXED CYCLOHEXATRIENE RING - COBALT-CATALYZED SYNTHESIS FROM HEXAETHYNYLBENZENE AND THERMAL RING-OPENING TO 1,2-5,6-9,10-TRIBENZO-3,4,7,8,11,12-HEXADEHYDRO[12]-ANNULENE [J].

DIERCKS, R ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3150-3152

← 1 2 3 4 5 →