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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  
dc.subject.classification
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