Iodine(I) and Silver(I) Complexes of Benzoimidazole and Pyridylcarbazole Derivatives

被引:19
作者
Taipale, Essi [1 ]
Siepmann, Marcel [1 ]
Khai-Nghi Truong [1 ]
Rissanen, Kari [1 ]
机构
[1] Univ Jyvaskyla, Dept Chem, POB 35,Survontie 9B, Jyvaskyla 40014, Finland
基金
芬兰科学院;
关键词
halogen(I); halogen bonds; NMR spectroscopy; supramolecular chemistry; X-ray crystallography; HALOGEN BOND; COORDINATION; SYMMETRY; REAGENTS;
D O I
10.1002/chem.202103152
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of iodine(I) complexes with either benzoimidazole or carbazole-derived sp(2) N-containing Lewis bases is described, as well as their corresponding silver(I) complexes. The addition of elemental iodine to the linear two-coordinate Ag(I) complexes produces iodine(I) complexes with a three-center four-electron (3c-4e) [N-I-N](+) bond. The H-1 and H-1-N-15 HMBC NMR studies unambiguously confirm the formation of the complexes in all cases via the [N-Ag-N](+)->[N-I-N](+) cation exchange, with the N-15 NMR chemical shift change between 94 to 111 ppm when compared to the free ligand. The single crystal X-ray crystallographic studies on eight I+ complexes revealed highly symmetrical [N-I-N](+) bonds with I-N bond distances of 2.21-2.26 angstrom and N-I-N angles of 177-180 degrees, whilst some of the corresponding Ag+ complexes showed a clear deviation from linearity with N-Ag-N angles of ca. 150 degrees and Ag-N bond distances of 2.09-2.18 angstrom.
引用
收藏
页码:17412 / 17419
页数:8
相关论文
共 50 条
[1]   Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4):: A versatile oxidizing reagent [J].
Barluenga, J ;
González-Bobes, F ;
Murguía, MC ;
Ananthoju, SR ;
González, JM .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (17) :4206-4213
[2]   AN EXPEDITIOUS AND GENERAL AROMATIC IODINATION PROCEDURE [J].
BARLUENGA, J ;
GONZALEZ, JM ;
GARCIAMARTIN, MA ;
CAMPOS, PJ ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) :1016-1017
[3]   Counterion influence on the N-I-N halogen bond [J].
Bedin, Michele ;
Karim, Alavi ;
Reitti, Marcus ;
Carlsson, Anna-Carin C. ;
Topic, Filip ;
Cetina, Mario ;
Pan, Fangfang ;
Havel, Vaclav ;
Al-Ameri, Fatima ;
Sindelar, Vladimir ;
Rissanen, Kari ;
Grafenstein, Jurgen ;
Erdelyi, Mate .
CHEMICAL SCIENCE, 2015, 6 (07) :3746-3756
[4]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[5]   Substituent Effects on the [N-I-N]+ Halogen Bond [J].
Carlsson, Anna-Carin C. ;
Mehmeti, Krenare ;
Uhrbom, Martin ;
Karim, Alavi ;
Bedin, Michele ;
Puttreddy, Rakesh ;
Kleinmaier, Roland ;
Neverov, Alexei A. ;
Nekoueishahraki, Bijan ;
Grafenstein, Jurgen ;
Rissanen, Kari ;
Erdelyi, Mate .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9853-9863
[6]   Solvent effects on halogen bond symmetry [J].
Carlsson, Anna-Carin C. ;
Uhrbom, Martin ;
Karim, Alavi ;
Brath, Ulrika ;
Grafenstein, Jurgen ;
Erdelyi, Mate .
CRYSTENGCOMM, 2013, 15 (16) :3087-3092
[7]   Symmetry of [N-X-N]+ halogen bonds in solution [J].
Carlsson, Anna-Carin C. ;
Grafenstein, Jurgen ;
Laurila, Jesse L. ;
Bergquist, Jonas ;
Erdelyi, Mate .
CHEMICAL COMMUNICATIONS, 2012, 48 (10) :1458-1460
[8]   The Halogen Bond [J].
Cavallo, Gabriella ;
Metrangolo, Pierangelo ;
Milani, Roberto ;
Pilati, Tullio ;
Priimagi, Arri ;
Resnati, Giuseppe ;
Terraneo, Giancarlo .
CHEMICAL REVIEWS, 2016, 116 (04) :2478-2601
[9]   IODODIPYRIDINIUM ION [J].
CREIGHTO.JA ;
HAQUE, I ;
WOOD, JL .
CHEMICAL COMMUNICATIONS, 1966, (23) :892-&
[10]   IODODIPYRIDINIUM ION [J].
CREIGHTON, JA ;
HAGUE, I ;
WOOD, JL .
CHEMICAL COMMUNICATIONS, 1966, (08) :229-+