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dc.contributor.author
Mancini, Pedro M. E.
dc.contributor.author
Della Rosa, Claudia D.
dc.contributor.author
Ormachea, Carla
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dc.contributor.author
Kneeteman, Maria Nelida
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dc.contributor.author
Domingo, Luis R.
dc.date.available
2017-05-04T19:50:03Z
dc.date.issued
2013
dc.identifier.citation
Mancini, Pedro M. E.; Della Rosa, Claudia D.; Ormachea, Carla; Kneeteman, Maria Nelida; Domingo, Luis R.; Experimental and theoretical studies on polar Diels–Alder reactions of 1-nitronaphathalene developed in ionic liquids; Royal Society of Chemistry; RSC Advances; 33; 2013; 13825-13834
dc.identifier.issn
2046-2069
dc.identifier.uri
http://hdl.handle.net/11336/15997
dc.description.abstract
The reactions between 1-nitronaphthalene 1 and two nucleophilic dienes, Danishefsky´s diene 2 and 1-trimethylsilyloxy-1,3-butadiene 3, to yield phenanthrenols 7 and 8 developed in protic and aprotic ionic liquids (ILs) with an imidazolium cation base permit to conclude that the reactions occur in better experimental conditions than in molecular solvents. The yields obtained with protic ILs are better than those observed with aprotic ILs. In this sense, the higher yields obtained with aprotic ILs, (working at 60ºC, 48 h) are comparable with the lower yields observed in protic ILs (60 ºC, 24 h). DFT calculations for the reaction of 1-nitronaphthalene 1 with diene 3, in the absence and in the presence of tetrafluoroborate of 1-metilimidazolium [HMIM] [BF4] as protic ILs, indicate that this reaction is a domino process that comprises two consecutive processes: i) a polar Diels-Alder (P-DA) reaction between 1 and 3, and ii) an elimination of nitroso acid 5 to yield dihydrophenanthrene 11. Thermodynamic calculations indicate that while the first reaction is the rate-determining step of this domino process, the nitroso acid elimination is the driving force responsible for the formation of dihydrophenanthrene 11. Implicit and explicit solvent effects indicate that while the hydrogen bond formation between HMIM and one oxygen atom of the nitro groups favour the two reactions, implicit solvent effects modelled by PCM decelerate the P-DA reaction by a large solvation of reagents. Finally, DFT analysis of reagents offers an explanation of the catalytic role of protic ILs in these P-DA reactions.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Diels-Alder
dc.subject
Nitronaphthalenes
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Ionic Liquid
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Dft
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Experimental and theoretical studies on polar Diels–Alder reactions of 1-nitronaphathalene developed in ionic liquids
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2017-04-17T19:25:57Z
dc.journal.number
33
dc.journal.pagination
13825-13834
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Londres
dc.description.fil
Fil: Mancini, Pedro M. E.. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
dc.description.fil
Fil: Della Rosa, Claudia D.. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
dc.description.fil
Fil: Ormachea, Carla. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Domingo, Luis R.. Universidad de Valencia; España
dc.journal.title
RSC Advances
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C3RA42042F
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/-/content/articlelanding/2013/ra/c3ra42042f#!divAbstract
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