Cross-dimerization of nitrosobenzenes in solution and in solid state

被引:26
作者
Halasz, Ivan [1 ]
Biljan, Ivana [1 ]
Novak, Predrag [1 ]
Mestrovic, Ernest [1 ]
Plavec, Janez [2 ]
Mali, Gregor [2 ]
Smrecki, Vilko [3 ]
Vancik, Hrvoj [1 ]
机构
[1] Univ Zagreb, Fac Sci, Dept Chem, HR-10000 Zagreb, Croatia
[2] Natl Inst Chem, SI-1115 Ljubljana, Slovenia
[3] NMR Ctr, Rudjer Boskovic Inst, HR-10000 Zagreb, Croatia
关键词
Nitrosobenzenes; Azodioxides; Solid-state dimerization; Solid solution; Co-crystalization; Cross-dimerization; C-NITROSO-COMPOUNDS; STRUCTURAL INVESTIGATIONS; REACTION-MECHANISMS; EQUILIBRIUM; SYSTEM; MODEL;
D O I
10.1016/j.molstruc.2008.07.035
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Cross-linking of nitrosobenzenes to heterodimers (azodioxides) when they are not sterically crowded with large groups in ortho-position was studied by NMR and FT-IR spectroscopy, X-ray crystallography as well as by cryogenic photolysis. It was found for the first time that cross-linked dimers (heterodimers) exist both in solution and in solid state and that they appear in the crystal together with homodimers. The system is used as a model for studying organic solid solution formation. The role of molecular packing in formation of a weak chemical bond is also discussed. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:19 / 25
页数:7
相关论文
共 25 条
[1]  
[Anonymous], CHEM INT ED ENGL
[2]   LOW-TEMPERATURE PROTON NUCLEAR MAGNETIC-RESONANCE AND ULTRAVIOLET-ABSORPTION SPECTRA AND PHOTOCHEMISTRY OF THE SYSTEM NITROSOBENZENE-AZODIOXYBENZENE AND ITS METHYL-DERIVATIVES [J].
AZOULAY, M ;
FISCHER, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (06) :637-642
[3]  
BARYUK VA, 1988, CHIMIA, V29, P270
[4]   A supramolecular approach to organic alloys:: Cocrystals and three- and four-component solid solutions of 1,4-diazabicyclo[2.2.2]octane and 4-X-phenols (X = Cl, CH3, Br) [J].
Dabros, Marta ;
Emery, Paul R. ;
Thalladi, Venkat R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4132-4135
[5]  
Farrugia L. J., 1999, J. Appl. Crystallogr, V32, P837, DOI [DOI 10.1107/S0021889812029111, DOI 10.1107/S0021889899006020]
[6]  
Farrujia LJ., 1997, J APPL CRYSTALLOGR, V30, P565, DOI [10.1107/S0021889897003117, DOI 10.1107/S0021889897003117]
[7]   Structural investigations of C-nitrosobenzenes. Part 2. NMR studies of monomer-dimer equilibria including restricted nitroso group rotation in monomers [J].
Fletcher, DA ;
Gowenlock, BG ;
Orrell, KG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (04) :797-803
[8]   Structural investigations of C-nitrosobenzenes .1. Solution state H-1 NMR studies [J].
Fletcher, DA ;
Gowenlock, BG ;
Orrell, KG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (11) :2201-2205
[9]   4-iodonitrosobenzene. Structural and spectroscopic studies of the monomeric solid and of previously unreported dimers [J].
Fletcher, DA ;
Gowenlock, BG ;
Orrell, KG ;
Sik, V ;
Hibbs, DE ;
Hursthouse, MB ;
Malik, KMA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (02) :191-197
[10]   Dinitroso and polynitroso compounds [J].
Gowenlock, BG ;
Richter-Addo, GB .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (09) :797-809