4-Iodonitrosobenzene. Structural and spectroscopic studies of the monomeric solid and of previously unreported dimers

Fletcher, Daniel A.; Gowenlock, B. G.; Orrell, Keith G.; Šik, Vladimír; Hibbs, David E.; Hursthouse, Michael B.; Malik, K. M. Abdul

doi:10.1039/p29960000191

Cited by 35 publications

(38 citation statements)

References 32 publications

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“…However, after sublimation this compound forms exclusively the stable monomers that do not dimerize spontaneously [13,30]. As it has been described in the experimental part of the paper by Fletcher, Gowenlock et al [35], the bright yellow crystals of E-azodioxy dimer of p-iodonitrosobenzene revert on heating to the green crystals of the monomer. This transformation could tentatively be explained by the higher stability of the monomer polymorph.…”

Section: Metathesis-like Reactionsmentioning

confidence: 84%

“…Such a system is simple because it includes the formation and/or breaking of only one chemical bond between two nitrogen atoms during the dimerization of C-nitroso compounds to the Z-or E-azodioxy dimers, or their subsequent dissociation to the starting monomers (Scheme 1) [32][33][34][35][36][37][38][39]. Although most of the aromatic C-nitroso compounds appear as Z-or E-azodioxides in solid state, certain nitrosobenzene derivatives, such as those with strong electron-donating substituents in the para-position (e.g., p-nitrosoanisoles and p-nitrosoanilines), prefer a monomeric form.…”

Section: Experimental and Conceptual Modelmentioning

confidence: 99%

“…The effect of the solid phase on the intermolecular selectivity is still an open question that stimulates future investigations. It must be pointed out that p-iodonitrosobenzene can be isolated in the form of E-dimer by crystallization from solution and that both Z-and E-dimers are present in equilibrium with monomers in solution at low temperatures [35]. However, after sublimation this compound forms exclusively the stable monomers that do not dimerize spontaneously [13,30].…”

Section: Metathesis-like Reactionsmentioning

confidence: 99%

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Aromatic C-Nitroso Compounds and Their Dimers: A Model for Probing the Reaction Mechanisms in Crystalline Molecular Solids

Biljan

Vančik

2017

Crystals

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This review is focused on the dimerization and dissociation of aromatic C-nitroso compounds and their dimers, the reactions that could be used as a convenient model for studying the thermal organic solid-state reaction mechanisms. This molecular model is simple because it includes formation or breaking of only one covalent bond between two nitrogen atoms. The crystalline molecular solids of nitroso dimers (azodioxides) dissociate by photolysis under the cryogenic conditions, and re-dimerize by slow warming. The thermal re-dimerization reaction is examined under the different topotactic conditions in crystals: disordering, surface defects, and phase transformations. Depending on the conditions, and on the molecular structure, aromatic C-nitroso compounds can associate to form one-dimensional polymeric structures and are able to self-assemble on gold surfaces.

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Section: Metathesis-like Reactionsmentioning

confidence: 84%

Section: Experimental and Conceptual Modelmentioning

confidence: 99%

Section: Metathesis-like Reactionsmentioning

confidence: 99%

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Aromatic C-Nitroso Compounds and Their Dimers: A Model for Probing the Reaction Mechanisms in Crystalline Molecular Solids

Biljan

Vančik

2017

Crystals

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“…respectively, but the orientation has little influence on the ring geometries [21]. The NHOH group strongly favours the pyramidal (sp 3 ) configuration over the planar (sp 2 ) form energetically, but small energy and geometry differences between the two orientations are found for the sp 3 form.…”

Section: 1mentioning

confidence: 94%

Trends in ortho-carboranes 1-X-2-R-1,2-C2B10H10 (R=Ph, Me) bearing an exo-CN-bonded substituent group (X=NO, NNR′ or NHR′′)

et al. 2009

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Publisher's copyright statement: NOTICE: this is the author's version of a work that was accepted for publication in Polyhedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reected in this document. Changes may have been made to this work since it was submitted for publication. A denitive version was subsequently published in Polyhedron, 28, 212, 2009Polyhedron, 28, 212, , 10.1016Polyhedron, 28, 212, /j.poly.2009 Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractThe preparation and crystal structures of four ortho-carboranyl-nitrogen compounds,

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“…The model that we have previously developed is based on the reactions of the substituted nitrosobenzenes in the crystal phase. The reaction system is in principle simple because it includes formation and/or breaking of only one chemical bond between two nitrogen atoms in dimerizations and dissociations of nitroso compounds (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Mechanochemically induced cross‐dimerizations of nitrosobenzenes. Kinetics and solid‐state isotope effects

Maganjić

Šolić

Milovac

et al. 2013

J of Physical Organic Chem

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Mechanical treatment (milling) of crystals of aromatic nitroso dimers (azodioxides) induces their dissociation and cross‐dimerizations. The mechanisms of these processes are discussed on the basis of kinetic studies and the solid‐state 15 N kinetic isotope effect, which is measured for the first time. By comparison with analogous processes in cocrystals and in melts, it appears that the reactions follow similar mechanism in which the surface deformations play the crucial role. The system can also be used as a model for a more general conceptual study of solid‐state reaction mechanisms. Copyright © 2013 John Wiley & Sons, Ltd.

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4-Iodonitrosobenzene. Structural and spectroscopic studies of the monomeric solid and of previously unreported dimers

Cited by 35 publications

References 32 publications

Aromatic C-Nitroso Compounds and Their Dimers: A Model for Probing the Reaction Mechanisms in Crystalline Molecular Solids

Aromatic C-Nitroso Compounds and Their Dimers: A Model for Probing the Reaction Mechanisms in Crystalline Molecular Solids

Trends in ortho-carboranes 1-X-2-R-1,2-C2B10H10 (R=Ph, Me) bearing an exo-CN-bonded substituent group (X=NO, NNR′ or NHR′′)

Mechanochemically induced cross‐dimerizations of nitrosobenzenes. Kinetics and solid‐state isotope effects

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