The contribution of ring conformational flexibility to the relative stability of isomeric cyclohexadienes

被引：6
|
作者：
Shishkin, OV
Leszczynski, J
机构：
[1] Jackson State Univ, Dept Chem, Computat Ctr Mol Modeling Struct & Interact, Jackson, MS 39217 USA
[2] Natl Acad Sci Ukraine, Inst Single Crystals, UA-310001 Kharkov, Ukraine
来源：
CHEMICAL PHYSICS LETTERS | 1999年 / 302卷 / 3-4期
关键词：
D O I：
10.1016/S0009-2614(99)00105-0
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The relative stability of isomeric cyclohexadienes was studied using density functional theory (B3LYP) and second-order Moller-Plesset perturbational method (MP2). It was demonstrated that higher conformational flexibility of dihydrocycles in 1,4-isomer results in additional stabilization of this molecules with respect to 1,3-cyclohexadiene. This fact is caused by the presence of low-frequency vibrations in 1,4-dihydrocycle which are populated at room temperature. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：262 / 266
页数：5
相关论文
共 50 条
  • [1] CONFORMATIONAL ANALYSIS .77. RELATIVE STABILITIES OF ISOMERIC ANDROSTANE RING SYSTEMS
    ALLINGER, NL
    WU, F
    TETRAHEDRON, 1971, 27 (21) : 5093 - &
  • [2] RELATIVE REACTIVITY OF ISOMERIC CYCLOHEXADIENES AND BICYCLO[4,1,0]HEPTENES
    MILVITSKAYA, EM
    KOVNER, OY
    PLATE, AF
    BINEVSKAYA, LI
    ZHURNAL ORGANICHESKOI KHIMII, 1977, 13 (03): : 547 - 551
  • [3] RELATIVE STABILITY OF ISOMERIC OLEFINS CONTAINING A 5-MEMBERED OR 6-MEMBERED RING
    GILAV, E
    SHABTAI, J
    CHEMISTRY & INDUSTRY, 1959, (52) : 1630 - 1630
  • [4] Conformational flexibility and rotation of the RING domain in activation of cullin–RING ligases
    Simin Rahighi
    Ivan Dikic
    Nature Structural & Molecular Biology, 2011, 18 : 863 - 865
  • [5] A Theoretical Investigation of the Relative Stability of Isomeric Dihydropyridines
    O. V. Shishkin
    R. I. Zubatyuk
    S. M. Desenko
    J. Leszczynski
    Chemistry of Heterocyclic Compounds, 2014, 50 : 327 - 335
  • [6] A Theoretical Investigation of the Relative Stability of Isomeric Dihydropyridines
    Shishkin, O. V.
    Zubatyuk, R. I.
    Desenko, S. M.
    Leszczynski, J.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (03) : 327 - 335
  • [7] Conformational flexibility of pyrimidine ring in adenine and related compounds
    Shishkin, OV
    Gorb, L
    Leszczynski, J
    CHEMICAL PHYSICS LETTERS, 2000, 330 (5-6) : 603 - 611
  • [8] CONFORMATIONAL FLEXIBILITY OF THE 12-MEMBERED SILOXANE RING
    TIMOFEEVA, TV
    MAKAROVA, NN
    DUBCHAK, IL
    STRUCHKOV, YT
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (08): : 1708 - 1711
  • [9] EXTREME CONFORMATIONAL FLEXIBILITY OF FURANOSE RING IN DNA AND RNA
    LEVITT, M
    WARSHEL, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) : 2607 - 2613
  • [10] Conformational flexibility and rotation of the RING domain in activation of cullin-RING ligases
    Rahighi, Simin
    Dikic, Ivan
    NATURE STRUCTURAL & MOLECULAR BIOLOGY, 2011, 18 (08) : 863 - 865
12345