Electrostatic control of aromatic stacking interactions

被引:280
|
作者
Cockroft, SL
Hunter, CA [1 ]
Lawson, KR
Perkins, J
Urch, CJ
机构
[1] Univ Sheffield, Krebs Inst Biomolec Res, Dept Chem, Ctr Chem Biol, Sheffield S3 7HF, S Yorkshire, England
[2] Jealotts Hill Int Res Ctr, Syngenta, Bracknell RG42 6EY, Berks, England
关键词
D O I
10.1021/ja050880n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A supramolecular approach has been used to investigate the free energies of intermolecular aromatic stacking interactions. Chemical double mutant cycles have been used to measure the effect of a range of substituents on face-to-face stacking interactions with phenyl and pentafluorophenyl rings. Electrostatic effects dominate the trends in interaction energy. Copyright © 2005 American Chemical Society.
引用
收藏
页码:8594 / 8595
页数:2
相关论文
共 50 条
  • [1] Investigation of the π-π stacking interactions without direct electrostatic effects of substituents: the aromatic∥aromatic and aromatic∥anti-aromatic complexes
    Ebrahimi, Ali
    Karimi, Pouya
    Akher, Farideh Badichi
    Behazin, Roya
    Mostafavi, Najmeh
    MOLECULAR PHYSICS, 2014, 112 (07) : 1047 - 1056
  • [2] Combined effects of electrostatic and π-π stacking interactions:: Selective binding of nucleotides and aromatic carboxylates by platinum(II) -: Aromatic ligand complexes
    Yajima, T
    Maccarrone, G
    Takani, M
    Contino, A
    Arena, G
    Takamido, R
    Hanaki, M
    Funahashi, Y
    Odani, A
    Yamauchi, O
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) : 3341 - 3352
  • [3] Substituent effects on aromatic stacking interactions
    Cockroft, Scott L.
    Perkins, Julie
    Zonta, Cristiano
    Adams, Harry
    Spey, Sharon E.
    Low, Caroline M. R.
    Vinter, Jeremy G.
    Lawson, Kevin R.
    Urch, Christopher J.
    Hunter, Christopher A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (07) : 1062 - 1080
  • [4] PLATINUM DNA INTERCALATOR MONONUCLEOTIDE ADDUCT FORMATION - COOPERATIVITY BETWEEN AROMATIC RING STACKING AND ELECTROSTATIC INTERACTIONS
    ODANI, A
    SHIMATA, R
    MASUDA, H
    YAMAUCHI, O
    INORGANIC CHEMISTRY, 1991, 30 (09) : 2133 - 2138
  • [5] A supramolecular system for quantifying aromatic stacking interactions
    Adams, H
    Hunter, CA
    Lawson, KR
    Perkins, J
    Spey, SE
    Urch, CJ
    Sanderson, JM
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (22) : 4863 - 4877
  • [6] Aromatic Stacking Interactions in Flavin Model Systems
    Nandwana, Vikas
    Samuel, Ifor
    Cooke, Graeme
    Rotello, Vincent M.
    ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (04) : 1000 - 1009
  • [7] Additivity of Substituent Effects in Aromatic Stacking Interactions
    Hwang, Jungwun
    Li, Ping
    Carroll, William R.
    Smith, Mark D.
    Pellechia, Perry J.
    Shimizu, Ken D.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (40) : 14060 - 14067
  • [8] THE ELECTROSTATIC CONTRIBUTION TO DNA BASE-STACKING INTERACTIONS
    FRIEDMAN, RA
    HONIG, B
    BIOPOLYMERS, 1992, 32 (02) : 145 - 159
  • [9] Enhanced Helical Folding of ortho-Phenylenes through the Control of Aromatic Stacking Interactions
    Mathew, Sanyo
    Crandall, Laura A.
    Ziegler, Christopher J.
    Hartley, C. Scott
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (47) : 16666 - 16675
  • [10] Parsing of the free energy of aromatic-aromatic stacking interactions in solution
    Kostjukov, Viktor V.
    Khomytova, Nina M.
    Hernandez Santiago, Adrian A.
    Cervantes Tavera, Anna-Maria
    Salas Alvarado, Julieta
    Evstigneev, Maxim P.
    JOURNAL OF CHEMICAL THERMODYNAMICS, 2011, 43 (10): : 1424 - 1434