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dc.contributor.author
Zanardi, Maria Marta
dc.contributor.author
Suarez, Alejandra Graciela
dc.contributor.author
Sarotti, Ariel Marcelo
dc.date.available
2018-06-28T17:26:04Z
dc.date.issued
2017-02
dc.identifier.citation
Zanardi, Maria Marta; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo; Determination of the Relative Configuration of Terminal and Spiroepoxides by Computational Methods: Advantages of the Inclusion of Unscaled Data; American Chemical Society; Journal of Organic Chemistry; 82; 4; 2-2017; 1873-1879
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/50399
dc.description.abstract
The assignment of the relative configuration of spiroepoxides or related quaternary carbon-containing oxiranes can be troublesome and difficult to achieve. The use of GIAO NMR shift calculations can provide helpful assistance in challenging cases of structural elucidation. In this regard, the DP4 probability is one of the most popular methods to be employed when only one set of experimental data is available, though modest results were obtained when dealing with spiroepoxides. Recently, we introduced an improved probability (DP4+) that includes the use of both scaled and unscaled NMR data computed at higher levels of theory. Here, we report a comprehensive study to explore the scope and limitations of the DP4+ methodology in the stereoassignment of terminal or spiroepoxides bearing a wide variety of molecular complexity and conformational freedom. The excellent levels of correct classification achieved were interpreted on the basis of a constructive compensation of errors upon using both scaled and unscaled proton and carbon data. The advantages of the DP4+ methodology in solving two case studies that could not be unequivocally assigned by NOE experiments are also provided.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by/2.5/ar/
dc.subject
Nmr
dc.subject
Oxiranes
dc.subject
Levoglucosenone
dc.subject
Computational Studies
dc.subject.classification
Otras Ciencias Químicas
dc.subject.classification
Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Determination of the Relative Configuration of Terminal and Spiroepoxides by Computational Methods: Advantages of the Inclusion of Unscaled Data
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-06-26T22:23:19Z
dc.journal.volume
82
dc.journal.number
4
dc.journal.pagination
1873-1879
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington DC
dc.description.fil
Fil: Zanardi, Maria Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Pontificia Universidad Católica Argentina ; Argentina
dc.description.fil
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.journal.title
Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acs.joc.6b02129
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b02129
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