Supramolecular Hierarchy among Halogen-Bond Donors

被引：199
|
作者：
Aakeroey, Christer B. [1 ]
Baldrighi, Michele [2 ]
Desper, John [1 ]
Metrangolo, Pierangelo [2 ]
Resnati, Giuseppe [2 ]
机构：
[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
[2] Politecn Milan, Dept Chem Mat & Chem Engn Giulio Natta, I-20133 Milan, Italy
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 48期
关键词：
crystal engineering; donor-acceptor systems; halogen bonding; self-assembly; supramolecular chemistry; C-13; NMR; HYDROGEN; COCRYSTALS; DIIODOACETYLENE; COMPLEXES; MOLECULES; CRYSTALS; SOLIDS; FORCES;
D O I：
10.1002/chem.201302162
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Through a combination of structural chemistry, vibrational spectroscopy, and theory, we have systematically examined the relative structure-directing importance of a series of ditopic halogen-bond (XB) donors. The molecular electrostatic potential surfaces of six XB donors were evaluated, which allowed for a charge-based ranking. Each molecule was then co-crystallized with 21 XB acceptors and the results have made it possible to map out the supramolecular landscape describing the competition between I/Br-ethynyl donors, perfluorinated I/Br donors, and I/Br-phenyl based donors. The results offer practical guidelines for synthetic crystal engineering driven by robust and directional halogen bonds.
引用
收藏
页码：16240 / 16247
页数：8
相关论文
共 50 条
  • [21] Halogen-Bond Assisted Photoinduced Electron Transfer
    Dereka, Bogdan
    Fureraj, Ina
    Rosspeintner, Arnulf
    Vauthey, Eric
    MOLECULES, 2019, 24 (23):
  • [22] Stacking Interactions: A Supramolecular Approach to Upgrade Weak Halogen Bond Donors
    Baykov, Sergey V.
    Ivanov, Daniil M.
    Kasatkina, Svetlana O.
    Galmes, Bartomeu
    Frontera, Antonio
    Resnati, Giuseppe
    Kukushkin, Vadim Y.
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (70)
  • [23] A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors
    Javaly, Nicole
    McCormick, Theresa M.
    Stuart, David R.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1428 - 1435
  • [24] Isomorphous Series of PdIII-Containing Halogen-Bond Donors Exhibiting CI/Br/I Triple Halogen Isostructural Exchange
    Buldakov, Alexander V.
    Kinzhalov, Mikhail A.
    Kryukova, Mariya A.
    Ivanov, Daniil M.
    Novikov, Alexander S.
    Smirnov, Andrey S.
    Starova, Galina L.
    Bokach, Nadezhda A.
    Kukushkin, Vadim Yu.
    CRYSTAL GROWTH & DESIGN, 2020, 20 (03) : 1975 - 1984
  • [25] Bidentate Chiral Bis(imidazolium)-Based Halogen-Bond Donors: Synthesis and Applications in Enantioselective Recognition and Catalysis
    Sutar, Revannath L.
    Engelage, Elric
    Stoll, Raphael
    Huber, Stefan M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (17) : 6806 - 6810
  • [26] Halogen-Bond Preferences in Co-crystal Synthesis
    Christer B. Aakeröy
    Tharanga K. Wijethunga
    John Desper
    Curtis Moore
    Journal of Chemical Crystallography, 2015, 45 : 267 - 276
  • [27] Bidentate Chiral Bis(imidazolium)-Based Halogen-Bond Donors: Synthesis and Applications in Enantioselective Recognition and Catalysis
    Sutar, Revannath L.
    Engelage, Elric
    Stoll, Raphael
    Huber, Stefan M.
    Advanced Materials, 2020, 132 (17): : 6872 - 6877
  • [28] Unexpected trends in halogen-bond based noncovalent adducts
    Huber, Stefan M.
    Jimenez-Izal, Elisa
    Ugalde, Jesus M.
    Infante, Ivan
    CHEMICAL COMMUNICATIONS, 2012, 48 (62) : 7708 - 7710
  • [29] Halogen-Bond Preferences in Co-crystal Synthesis
    Aakeroey, Christer B.
    Wijethunga, Tharanga K.
    Desper, John
    Moore, Curtis
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2015, 45 (06) : 267 - 276
  • [30] 5-Iodo-1,2,3-triazolium-based multidentate halogen-bond donors as activating reagents
    Kniep, Florian
    Rout, Laxmidhar
    Walter, Sebastian M.
    Bensch, Heide K. V.
    Jungbauer, Stefan H.
    Herdtweck, Eberhardt
    Huber, Stefan M.
    CHEMICAL COMMUNICATIONS, 2012, 48 (74) : 9299 - 9301
12345