Halogen bonding: a general route in anion recognition and coordination

被引:422
作者
Cavallo, Gabriella [1 ]
Metrangolo, Pierangelo [1 ,2 ]
Pilati, Tullio [3 ]
Resnati, Giuseppe [1 ,2 ]
Sansotera, Maurizio [1 ]
Terraneo, Giancarlo [1 ,2 ]
机构
[1] Politecn Milan, DCMIC G Natta, NFMLab, I-20131 Milan, Italy
[2] IIT PoliMI, Ctr Nano Sci & Technol, I-20133 Milan, Italy
[3] Univ Milan, CNRS, Inst Mol Sci & Technol, I-20133 Milan, Italy
关键词
NUCLEIC ACID INTERACTIONS; MONOPHOSPHATE CRYSTALLINE COMPLEX; NITROGEN-BASE LIGANDS; X-RAY; MOLECULAR-STRUCTURE; ATOMIC RESOLUTION; HYDROGEN-BOND; STRUCTURAL SYSTEMATICS; SILVER(I) COMPLEXES; SELF-ASSEMBLIES;
D O I
10.1039/b926232f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This critical review describes how halocarbons can function as effective binding sites of anions via halogen bonding, the noncovalent interaction whereby halogen atoms accept electron density. The focus is on the binding and coordination of oxyanions, by far the most numerous class of anions in organic chemistry. It is shown how a large variety of inorganic and organic oxyanions can form discrete adducts and 1D, 2D, or 3D supramolecular networks with chloro-, bromo-, and iodocarbons. Specific examples are discussed in order to identify new supramolecular synthons based on halogen bonding and to outline some general principles for the design of effective and selective receptors based on this interaction. The interaction allows for several other anions to self-assemble with halocarbons and mention is also given to the halogen bonding-based coordination of halides, polycyano- and polyoxometallates (72 references).
引用
收藏
页码:3772 / 3783
页数:12
相关论文
共 214 条
[1]   Halide anions driven self-assembly of haloperfluoroarenes: Formation of one-dimensional non-covalent copolymers [J].
Abate, Antonio ;
Biella, Serena ;
Cavallo, Gabriella ;
Meyer, Franck ;
Neukirch, Hannes ;
Metrangolo, Pierangelo ;
Pilati, Tullio ;
Resnati, Giuseppe ;
Terraneo, Giancarlo .
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (12) :1171-1177
[2]   ANTINEOPLASTIC AGENTS .27. SINGLE CRYSTAL X-RAY STRUCTURES OF CHEMOTHERAPEUTIC AGENTS .3. STRUCTURE OF 1,4-DIAZABICYCLO[2.2.1]HEPTANES, A NEW HETEROCYCLIC RING SYSTEM [J].
ABRAHAM, DJ ;
ROSENSTEIN, RD ;
PETTIT, GR .
JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (11) :1141-+
[3]   An anionic weak acceptor 2-aminomethylsulfo-3,5,6-trichloro-1, 4-benzoquinone and its BEDT-TTF-based charge-transfer salts [J].
Akutsu, Hiroki ;
Yamada, Jun-ichi ;
Nakatsuji, Shin'ichi ;
Turner, Scott S. .
SOLID STATE COMMUNICATIONS, 2007, 144 (3-4) :144-147
[4]   X-ray crystallographic study of copper(II), cobalt(II) and silver(I) complexes of ligands containing two oxine subunits linked by xylylene spacer groups [J].
Al-Mandhary, MRA ;
Steel, PJ .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (02) :329-334
[5]   Laying traps for elusive prey: Recent advances in the non-covalent binding of anions [J].
Atwood, JL ;
Holman, KT ;
Steed, JW .
CHEMICAL COMMUNICATIONS, 1996, (12) :1401-1407
[6]   MACROCYCLES CONTAINING TIN - SYNTHESES OF SYMMETRICAL MACROCYCLES CONTAINING 2 OR 4 DIPHENYLSTANNA UNITS [J].
AZUMA, Y ;
NEWCOMB, M .
ORGANOMETALLICS, 1984, 3 (01) :9-14
[7]   Interfacial Behavior of Perchlorate versus Chloride Ions in Aqueous Solutions [J].
Baer, Marcel D. ;
Kuo, I-Feng William ;
Bluhm, Hendrik ;
Ghosal, Sutapa .
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (48) :15843-15850
[8]   Hydrogen-bonding patterns in substituted oxines. Redetermination of 8-hydroxy-7-iodoquinoline-5-sulfonic acid [J].
Balasubramanian, T ;
Muthiah, PT .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1996, 52 :2072-2073
[9]   Vibrational properties and X-ray crystal structure of 3-iodo-2,6-dimethyl-4-nitropyridine N-oxide [J].
Ban-Oganowska, H ;
Hanuza, J ;
Maczka, M ;
Waskowska, A ;
van der Maas, JH ;
Oganowski, W ;
Talik, Z .
VIBRATIONAL SPECTROSCOPY, 2001, 26 (01) :83-97
[10]   Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 1: 2-pyridinylguanidines [J].
Barber, CG ;
Dickinson, RP ;
Horne, VA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (02) :181-184