Noncovalent Isotope Effect for Guest Encapsulation in Self-Assembled Molecular Capsules

被引:39
|
作者
Haino, Takeharu [1 ]
Fukuta, Katsunori [1 ]
Iwamoto, Hajime [1 ]
Iwata, Suehiro [2 ,3 ,4 ]
机构
[1] Hiroshima Univ, Grad Sch Sci, Dept Chem, Higashihiroshima 7398526, Japan
[2] Hiroshima Univ, Ctr Quantum Life Sci, Higashihiroshima 7398526, Japan
[3] Hiroshima Univ, Grad Sch, Higashihiroshima 7398526, Japan
[4] Toyota Phys & Chem Res Inst Nagakute, Aichi 4801192, Japan
关键词
isotope effects; methyl internal rotation; molecular recognition; self-assembly; van't Hoff plots; PROBE; COMPLEXATION; BONDS;
D O I
10.1002/chem.200902526
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
"Chemical Equation Presented" Deuteration leads to stronger binding: Deuterated guests bind within the confined space of the molecular capsule more preferentially than protiated guests (see scheme). The van 't Hoff analysis of the competitive association reveals that the preferential binding of the deuterated guests is driven by enthalpy and opposed by entropy. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:13286 / 13290
页数:5
相关论文
共 50 条
  • [41] Control of stilbene conformation and fluorescence in self-assembled capsules
    Ams, Mark R.
    Ajami, Dariush
    Craig, Stephen L.
    Yang, Jye-Shane
    Rebek, Julius, Jr.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5
  • [42] Are they truly capsules? Computed structures of self-assembled molecular complexes in polar solvents.
    Mardis, KL
    Hoge, EM
    Larson, KC
    Nguyen, LPT
    Smith, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U221 - U221
  • [43] Selective Stabilization of Self-Assembled Hydrogen-Bonded Molecular Capsules Through π-π Interactions
    Tiefenbacher, Konrad
    Rebek, Julius, Jr.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 2914 - 2917
  • [44] Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules
    Huerta, Elisa
    Artin Serapian, Stefano
    Santos, Eva
    Cequier, Enrique
    Bo, Carles
    de Mendoza, Javier
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (38) : 13496 - 13505
  • [45] Tailoring of self-assembled capsules for separation processes.
    Atwood, JL
    Barbour, LJ
    Orr, GW
    Raston, CL
    Webb, HR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U738 - U738
  • [46] Trinuclear Cu(II) capsules self-assembled by nitrilotripropionate
    Brana, Emiliano
    Mendoza, Carolina
    Vitoria, Pablo
    Gonzalez-Platas, Javier
    Dominguez, Sixto
    Kremer, Carlos
    INORGANICA CHIMICA ACTA, 2014, 417 : 192 - 200
  • [47] Tunable enforced cavities inside self-assembled capsules
    Maehara, Takeshi
    Sekiya, Ryo
    Harada, Kentaro
    Haino, Takeharu
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (10): : 1561 - 1566
  • [48] Emergent mechanical properties of self-assembled polymeric capsules
    Castellano, RK
    Clark, R
    Craig, SL
    Nuckolls, C
    Rebek, J
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (23) : 12418 - 12421
  • [49] Self-assembled lipid nanotube hosts: The dimension control for encapsulation of nanometer-scale guest substances
    Shimizu, Toshimi
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (17) : 5137 - 5152
  • [50] Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions
    Corbellini, F
    Fiammengo, R
    Timmerman, P
    Crego-Calama, M
    Versluis, K
    Heck, AJR
    Luyten, I
    Reinhoudt, DN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) : 6569 - 6575