Nitrosobenzene cross-dimerization: Structural selectivity in solution and in solid state

被引：13

作者：

Biljan, Ivana ^{[1
]}

Cvjetojevic, Gorana ^{[1
]}

Smrecki, Vilko ^{[2
]}

Novak, Predrag ^{[1
]}

Mali, Gregor ^{[3
]}

Plavec, Janez ^{[3
]}

Babic, Darko ^{[2
]}

Mihalic, Zlatko ^{[1
]}

Vancik, Hrvoj ^{[1
]}

机构：

[1] Univ Zagreb, Fac Sci, Dept Chem, HR-10000 Zagreb, Croatia

[2] Rudjer Boskovic Inst, HR-10000 Zagreb, Croatia

[3] Natl Inst Chem, SI-1115 Ljubljana, Slovenia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2010年 / 979卷 / 1-3期

关键词：

Nitrosobenzenes; Azodioxides; Cross-dimerization; Selectivity;

D O I：

10.1016/j.molstruc.2010.05.034

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：

Possibility of nitrosobenzenes to form dimeric molecular structures (azodioxides) is used as a model for intermolecular selectivity investigations in solution as well as in solid state. Cross-dimerization of different combinations of p- and m-substituted nitrosobenzene pairs was studied by variable temperature H-1 NMR, solid-state NMR (CP MAS), IR, and ab initio calculations. It is evident that p-nitronitrosobenzene behaves nonselectively because it forms dimers with all the studied nitrosobenzene partners. In contrast, p-methoxynitrosobenzene in most cases does not form dimers. The evidence that ability to form dimers is different in solution than in the solid state can be explained by influence of molecular arrangements in the crystal lattice. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：22 / 26

页数：5

共 21 条

[11] AZODIOXIDE RADICAL CATIONS [J].

GREER, ML ;

SARKER, H ;

MENDICINO, ME ;

BLACKSTOCK, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) :10460-10467

[12] Solid-state reaction mechanisms in monomer-dimer interconversions of p-bromonitrosobenzene.: Single-crystal-to-single-crystal photodissociation and formation of new non-van der Waals close contacts [J].

Halasz, I ;

Mestrovic, E ;

Cicak, H ;

Mihalic, Z ;

Vancik, H .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8461-8467

[13] Cross-dimerization of nitrosobenzenes in solution and in solid state [J].

Halasz, Ivan ;

Biljan, Ivana ;

Novak, Predrag ;

Mestrovic, Ernest ;

Plavec, Janez ;

Mali, Gregor ;

Smrecki, Vilko ;

Vancik, Hrvoj .

JOURNAL OF MOLECULAR STRUCTURE, 2009, 918 (1-3) :19-25

[14]

ORRELL KG, 1990, J CHEM SOC PERK T 2, P1297

[15] NMR-STUDY OF THE MONOMER-DIMER EQUILIBRIA OF DIMETHYLNITROSOBENZENES IN SOLUTION - IDENTIFICATION OF MIXED AZODIOXY DIMERIC SPECIES [J].

ORRELL, KG ;

STEPHENSON, D ;

RAULT, T .

MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (04) :368-376

[16] STUDY OF THE MONOMER DIMER EQUILIBRIUM OF NITROSOBENZENE USING MULTINUCLEAR ONE-DIMENSIONAL AND TWO-DIMENSIONAL NMR TECHNIQUES [J].

ORRELL, KG ;

SIK, V ;

STEPHENSON, D .

MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (11) :1007-1011

[17] Efficient preparation of nitrosoarenes for the synthesis of azobenzenes [J].

Priewisch, B ;

Rück-Braun, K .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2350-2352

[18]

Simunic-Meznaric V, 2005, CROAT CHEM ACTA, V78, P511

[19] CIS AZOXY ALKANES .6. CIS AZO N,N'-DIOXIDE SYNTHESIS AND IMPORTANCE OF ENTROPY IN NITROSOALKANE-AZO DIOXIDE EQUILIBRIUM [J].

SNYDER, JP ;

HEYMAN, ML ;

SUCIU, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (10) :1395-1405

[20] X-RAY STRUCTURE AND NORMAL COORDINATE ANALYSIS OF PARA-NITROSOANISOLE [J].

TALBERG, HJ .

ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1979, 33 (04) :289-296

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