Charge-Transfer Adducts of Chalcogenourea Derivatives of N-Heterocyclic Carbenes with Iodine Monochloride

被引:3
作者
Saab, Marina [1 ]
Nahra, Fady [2 ,3 ]
Van Hecke, Kristof [1 ]
机构
[1] Univ Ghent, Dept Chem, XStruct, Krijgslaan 281,Bldg S3, B-9000 Ghent, Belgium
[2] Univ Ghent, Dept Chem, Krijgslaan 281,Bldg S3, B-9000 Ghent, Belgium
[3] VITO Flemish Inst Technol Res, Boeretang 200, B-2400 Mol, Belgium
关键词
selenourea; thiourea; N-heterocyclic carbene; iodine monochloride; RAY CRYSTAL-STRUCTURES; STRUCTURAL-CHARACTERIZATION; MOLECULAR ADDUCTS; DIIODINE ADDUCTS; COMPLEXES; MECHANISM; DONORS; SE; BENZIMIDAZOLE-2-THIONE; THIOAMIDES;
D O I
10.3390/M1344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this communication, we investigate the reaction between seleno- and thiourea, derived from N-heterocyclic carbenes, with the interhalogen iodine monochloride. The formation of all three products was confirmed by NMR spectroscopy, while single-crystal X-ray analyses were able to establish a charge-transfer coordination type, which showed a linear Se/S-I-Cl arrangement, for all adducts formed. Based on a detailed crystallographic analysis, we can deduce the zwitterionic character of these compounds.
引用
收藏
页数:8
相关论文
共 29 条
[1]  
[Anonymous], 2019, CrysAlisPro Software system
[2]   Synthesis, X-ray characterization and study of new ionic complexes of 2-pyridone, obtained by oxidation with I2 [J].
Antoniadis, CD ;
Hadjikakou, SK ;
Hadjiliadis, N ;
Kubicki, M ;
Butler, IS .
NEW JOURNAL OF CHEMISTRY, 2005, 29 (05) :714-720
[3]   Synthesis, X-ray characterisation and studies of the new ionic complex [bis(pyridin-2-yl) disulfide] triiodide, obtained by oxidation of 2-mercaptopyridine with I2 -: Implications in the mechanism of action of antithyroid drugs [J].
Antoniadis, CD ;
Hadjikakou, SK ;
Hadjiliadis, N ;
Kubicki, M ;
Butler, IS .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (21) :4324-4329
[4]   Charge-transfer adducts between donors containing chalcogens (S and Se) and di-iodine: solution studies [J].
Aragoni, MC ;
Arca, M ;
Devillanova, FA ;
Garau, A ;
Isaia, F ;
Lippolis, V ;
Verani, G .
COORDINATION CHEMISTRY REVIEWS, 1999, 184 :271-290
[5]  
Aragoni MC, 2001, CHEM-EUR J, V7, P3122, DOI 10.1002/1521-3765(20010716)7:14<3122::AID-CHEM3122>3.0.CO
[6]  
2-H
[7]   The reactions of sulfur and selenium donor molecules with dihalogens and interhalogens [J].
Boyle, PD ;
Godfrey, SM .
COORDINATION CHEMISTRY REVIEWS, 2001, 223 :265-299
[8]   Synthesis, structural characterization, and computational studies of novel diiodine adducts with the heterocyclic thioamides N-methylbenzothiazole-2-thione and benzimidazole-2-thione:: Implications with the mechanism of action of antithyroid drugs [J].
Corban, GJ ;
Hadjikakou, SK ;
Hadjiliadis, N ;
Kubicki, M ;
Tiekink, ERT ;
Butler, IS ;
Drougas, E ;
Kosmas, AM .
INORGANIC CHEMISTRY, 2005, 44 (23) :8617-8627
[9]   CHARGE-TRANSFER COMPLEXES OF BENZOXAZOLE-2(3H)-THIONE AND BENZOXAZOLE-2(3H)-SELONE WITH DIIODINE - X-RAY CRYSTAL-STRUCTURE OF BENZOXAZOLE-2(3H)-THIONE BIS(DIIODINE) [J].
CRISTIANI, F ;
DEVILLANOVA, FA ;
ISAIA, F ;
LIPPOLIS, V ;
VERANI, G ;
DEMARTIN, F .
POLYHEDRON, 1995, 14 (20-21) :2937-2943
[10]  
Daga V, 2002, EUR J INORG CHEM, P1718