ELECTRONIC-STRUCTURE OF BENZO[3,4]CYCLOBUTA[1,2]CYCLOHEPTENYL IONS - THE AROMATICITY TROPICITY DILEMMA

被引：1

作者：

EDLUND, U ^{[1
]}

JOHNELS, D ^{[1
]}

ELIASSON, B ^{[1
]}

TROGEN, L ^{[1
]}

机构：

[1] NATL DEF RES ESTAB,DEPT NBC DEF RES,S-90182 UMEA,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An H-1 and C-13 NMR study of the benzo[3,4]cyclobuta[1,2]cycloheptenyl cation and anion has been undertaken in order to unravel the electronic structure of these species. The formal addition of two electrons to the cation can be seen as a conversion of a slightly diatropic and aromatic cation into an unstable, highly diatropic but antiaromatic anion. Self-consistent iterative Huckel, MNDO, and AM1 as well as graph-theoretical ring current calculations were carried out in order to clarify this confusion. Comparisons to the isoelectronic biphenylene and biphenylene dianion are especially revealing.

引用

页码：2020 / 2024

页数：5

共 50 条

[41] MAGNETISM AND ELECTRONIC-STRUCTURE OF 3D AND 4D IONS IN METALS
RIEGEL, D
GROSS, KD
PHYSICA B, 1990, 163 (1-3): : 678 - 682
[42] PHOTOOXIDATION OF 2,3,7,8-TETRAKIS(TRIMETHYLSILYL)BENZO[3,4]CYCLOBUTA[1,2-B]-BIPHENYLENEIN THE PRESENCE OF OXYGEN - UNUSUAL CLEAVAGE OF A BENZENE-RING TO GENERATE AN ALKYNE UNIT
MESTDAGH, H
VOLLHARDT, KPC
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (04) : 281 - 282
[43] CRYSTAL STRUCTURE OF BENZO[1,2 - 4,5]DICYCLOBUTENE
LAWRENCE, JL
MACDONAL.SG
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1969, B 25 : 978 - &
[44] 6a,6b,12a,12b-Tetrahydrocycloocta[3,4]cyclobuta[1,2][8]annulene
Mehta, G
Vanessa, G
Islam, K
Venkatesan, K
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2004, 60 : O90 - O93
[45] SYNTHESIS AND ELECTRONIC-STRUCTURE OF POTENTIALLY VALENCE ISOMERIC 1,2-DITHIOLYLIUM-4-OLATES
MAYER, R
FABIAN, J
VIOLA, H
JAKISCH, L
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 31 (1-2): : 109 - 122
[46] Thermal characterization of butadiene-isoprene copolymers with a 1,2/3,4 structure
Bertini, F
Canetti, M
De Chirico, A
Ricci, G
JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 88 (12) : 2737 - 2743
[47] HEXAHYDRO-4B,6,7,8,9,9A 5H-BENZO[3,4]CYCLOBUTA[1,2]CYCLOHEPTENOL-1-CIS, C13H16O
COURTOIS, PA
PESMEPICHON, V
CARRE, MC
CAUBERE, P
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (MAY) : 793 - 795
[48] ELECTRONIC-STRUCTURE OF ZN1-XCUXCR2SE4
JUSZCZYK, S
PHYSICA B, 1989, 161 (1-3): : 183 - 185
[49] SYNTHESIS OF 3,4-BENZO-1,1,2,2-TETRAMETHYL-1,2-DISILACYCLOPENTENE
TSUI, FP
ZON, G
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 70 (01) : C3 - C4
[50] ELECTRON SPIN RESONANCE SPECTRA OF NEGATIVE IONS OF 1,2-BENZPYRENE - 1,2 - 3,4-DIBENZANTHRACENF - AND 3,4-BENZPHENANTHRENE
GRIFFITH, OF
POOLE, CP
SPECTROCHIMICA ACTA PART A-MOLECULAR SPECTROSCOPY, 1969, A 25 (08): : 1463 - &

← 1 2 3 4 5 →