Isolated pentagon rule in buckybowls: a computational study on thermodynamic stabilities and bowl-to-bowl inversion barriers

被引：22

作者：

Dinadayalane, TC ^{[1
]}

Sastry, GN ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Mol Modelling Grp, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 42期

关键词：

bowl-to-bowl inversion barrier; relative stability; density functional theory; isolated pentagon rule; buckybowls;

D O I：

10.1016/j.tet.2003.09.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Computations on a series of sumanene and pinakene isomers reveal that the isolated pentagon species are found to be more stable than non-isolated pentagon structures. However, the present study indicates that there is no correlation between the bowl-to-bowl inversion barrier and the relative stability. Unexpectedly, the least stable isomer has the lowest bowl-to-bowl inversion barrier in pinakene isomers. Thus, curvature cannot be taken as a measure to evaluate the stability of buckybowls. The relative energy ordering and HOMO-LUMO gap correlate well in the series of pinakene isomers considered. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8347 / 8351

页数：5

共 40 条

[1] Is peri hydrogen repulsion responsible for flattening buckybowls?: The effect of ring annelation to the rim of corannulene [J].

Dinadayalane, TC ;

Deepa, S ;

Sastry, GN .

TETRAHEDRON LETTERS, 2003, 44 (24) :4527-4529

[2] An assessment of semiempirical (MNDO, AM1 and PM3) methods to model buckybowls [J].

Dinadayalane, TC ;

Sastry, GN .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2002, 579 :63-72

[3] Ring closure synthetic strategies toward buckybowls:: benzannulation versus cyclopentannulation [J].

Dinadayalane, TC ;

Priyakumar, UD ;

Sastry, GN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (01) :94-101

[4] Structure-energy relationships in curved polycyclic aromatic hydrocarbons: Study of benzocorannulenes [J].

Dinadayalane, TC ;

Sastry, GN .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4605-4607

[5] Theoretical studies on the effect of sequential benzannulation to corannulene [J].

Dinadayalane, TC ;

Priyakumar, UD ;

Sastry, GN .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2001, 543 :1-10

[6] Synthetic strategies toward buckybowls and C60:: benzannulation is remarkably facile compared to cyclopentannulation [J].

Dinadayalane, TC ;

Sastry, GN .

TETRAHEDRON LETTERS, 2001, 42 (36) :6421-6423

[7]

FRISCH MJ, 2001, GAUSSIAN 98 REVISION

[8] PI-ELECTRONS IN 3 DIMENSIONS [J].

HADDON, RC .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (06) :243-249

[9] MEASURE OF NONPLANARITY IN CONJUGATED ORGANIC-MOLECULES - WHICH STRUCTURALLY CHARACTERIZED MOLECULE DISPLAYS THE HIGHEST DEGREE OF PYRAMIDALIZATION [J].

HADDON, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3385-3389

[10] PYRAMIDALIZATION - GEOMETRICAL INTERPRETATION OF THE PI-ORBITAL AXIS VECTOR IN 3 DIMENSIONS [J].

HADDON, RC .

JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (14) :3719-3720

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