Mobius aromaticity and delocalization

被引:293
作者
Rzepa, HS [1 ]
机构
[1] Univ London Imperial Coll Sci & Technol, Dept Chem, London SW7 2AY, England
关键词
D O I
10.1021/cr030092l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The evaluations done by scientists in 1993 demonstrated that pericyclic transition states proceeding with half-twist Mobius topology exhibit aromatic properties. The molecules sustaining Mobius electronic conjugation are important because of their chiral nature. In particular, electronic delocalization in such systems manifest itself not only in typically aromaticbond lengths but also in the degree of localization of the 180° phase shift in the orbital topology. Because of the chiral nonplanar symmetry of Mobius rings compared to the Huckel systems, reliable quantitative measures of their properties relative contributions of the π and σ electronic frameworks remain to be developed.
引用
收藏
页码:3697 / 3715
页数:19
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共 127 条
[11]  
Berger C, 1998, ANGEW CHEM INT EDIT, V37, P1850, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1850::AID-ANIE1850>3.0.CO
[12]  
2-B
[13]   Unprecedented catalytic enantioselective trapping of arene oxides with dialkylzinc reagents [J].
Bertozzi, F ;
Crotti, P ;
Del Moro, F ;
Feringa, BL ;
Macchia, F ;
Pineschi, M .
CHEMICAL COMMUNICATIONS, 2001, (24) :2606-2607
[14]   Electrocyclic ring openings of 2-furylcarbene and related carbenes: A comparison between pseudopericyclic and coarctate reactions [J].
Birney, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :10917-10925
[15]   All-metal aromaticity and antiaromaticity [J].
Boldyrev, AI ;
Wang, LS .
CHEMICAL REVIEWS, 2005, 105 (10) :3716-3757
[16]  
Breslow R., 1965, Chem. Eng. News Archive, V43, P90, DOI 10.1021/cen-v043n026.p090
[17]   The magnetic Mobius strip: Synthesis, structure, and magnetic studies of odd-numbered antiferromagnetically coupled wheels [J].
Cador, O ;
Gatteschi, D ;
Sessoli, R ;
Larsen, FK ;
Overgaard, J ;
Barra, AL ;
Teat, SJ ;
Timco, GA ;
Winpenny, REP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5196-5200
[18]   Mobius aromaticity in [12]annulene: Cis-trans isomerization via twist-coupled bond shifting [J].
Castro, C ;
Karney, WL ;
Valencia, MA ;
Vu, CMH ;
Pemberton, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9704-9705
[19]   Aromaticity with a twist:: Mobius [4n]annulenes [J].
Castro, C ;
Isborn, CM ;
Karney, WL ;
Mauksch, M ;
Schleyer, PV .
ORGANIC LETTERS, 2002, 4 (20) :3431-3434
[20]   Investigation of a putative Mobius aromatic hydrocarbon. The effect of benzannelation on Mobius [4n]annulene aromaticity [J].
Castro, C ;
Chen, ZF ;
Wannere, CS ;
Jiao, HJ ;
Karney, WL ;
Mauksch, M ;
Puchta, R ;
Hommes, NJRV ;
Schleyer, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) :2425-2432