Aromaticity with a twist:: Mobius [4n]annulenes

被引:83
|
作者
Castro, C
Isborn, CM
Karney, WL
Mauksch, M
Schleyer, PV
机构
[1] Univ San Francisco, Dept Chem, San Francisco, CA 94117 USA
[2] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany
[3] Univ Erlangen Nurnberg, Comp Chem Ctr, D-91054 Erlangen, Germany
[4] Univ Georgia, Dept Chem, Athens, GA 30602 USA
关键词
D O I
10.1021/ol026610g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Aromatic Mobius [4n]annulenes with 4n pi electrons, originally conceived by Heilbronner, are characterized computationally. These (CH)(12), (CH)(16), and (CH)(20) minima have nearly equal C-C bond lengths, small twist angles around the rings, and magnetic properties (NICS, nucleus-independent chemical shifts-see above at various positions in [16]annulene-and magnetic susceptibility exaltations) indicating significantly diatropic ring currents. The Mobius forms are not the most stable isomers but may contribute significantly to the chemistry of these annulenes.
引用
收藏
页码:3431 / 3434
页数:4
相关论文
共 50 条
  • [21] Protonated [4n]π and [4n+2]π Octaphyrins Choose Their Mobius/Huckel Aromatic Topology
    Lim, Jong Min
    Shin, Jae-Yoon
    Tanaka, Yasuo
    Saito, Shohei
    Osuka, Atsuhiro
    Kim, Dongho
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 3105 - 3114
  • [23] Aromaticity of ring carbo-mers of [N]annulenes and [N]cycloalkanes
    Soncini, Alessandro
    Fowler, Patrick W.
    Lepetit, Christine
    Chauvin, Remi
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2008, 10 (07) : 957 - 964
  • [24] Ring-current aromaticity in triplet states of 4n π electron monocycles
    Fowler, PW
    Steiner, E
    Jenneskens, LW
    CHEMICAL PHYSICS LETTERS, 2003, 371 (5-6) : 719 - 723
  • [25] A THEORETICAL SCHEME OF ANNULENES AROMATICITY
    LESKA, J
    LOOS, D
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1984, 49 (04) : 920 - 935
  • [26] HUCKEL THEORY AND AROMATICITY OF ANNULENES
    COCORDANO, M
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1977, 284 (12): : 441 - 444
  • [27] RING CURRENT AND AROMATICITY IN ANNULENES
    VERBRUGGEN, A
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1982, 91 (10): : 865 - 868
  • [28] The aromaticity of dicupra[10] annulenes
    Grande-Aztatzi, Rafael
    Mercero, Jose M.
    Matito, Eduard
    Frenking, Gernot
    Ugalde, Jesus M.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2017, 19 (14) : 9669 - 9675
  • [29] Polycyclic Hydrocarbons from [4n]Annulenes: Correlation versus Hybridization Forces in the Formation of Diradicaloids
    Moles Quintero, Sergio
    Haley, Michael M.
    Kertesz, Miklos
    Casado, Juan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (44)
  • [30] Mobius aromaticity and delocalization
    Rzepa, HS
    CHEMICAL REVIEWS, 2005, 105 (10) : 3697 - 3715