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dc.contributor.author
Ghiviriga, Ion
dc.contributor.author
Zhang, Lianhao
dc.contributor.author
Martinez, Henry
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Contreras, Ruben Horacio
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Tormena, Cláudio F.
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Nodin, Laura
dc.contributor.author
Dolbier Jr., William R.
dc.date.available
2018-08-24T16:58:43Z
dc.date.issued
2011-02
dc.identifier.citation
Ghiviriga, Ion; Zhang, Lianhao; Martinez, Henry; Contreras, Ruben Horacio; Tormena, Cláudio F.; et al.; 19F chemical shifts, coupling constants and conformational preferences in monosubstituted perfluoroparacyclophanes; John Wiley & Sons Ltd; Magnetic Resonance in Chemistry; 49; 3; 2-2011; 93-105
dc.identifier.issn
0749-1581
dc.identifier.uri
http://hdl.handle.net/11336/56984
dc.description.abstract
In the process of studying the chemistry of perfluoro[2.2]paracyclophanes (PFPCs), a novel class of compounds, it became necessary to identify some disubstituted products. To achieve this goal, we characterize in this work some monosubstituted PFPCs, identifying their 19F-19F coupling patterns, and establishing a methodology for the assignment of their 19F chemical shifts. The pattern of coupling constants indicates a skewed geometry in which the upper deck moves towards or away from the substituent, depending on the substituent electron-donor character and size. Quantum chemical calculations, performed at the HF/6-311 + G(d,p)//B3LYP/EPR-III level of theory, confirmed the conformations inferred from coupling constants and reproduced well the values of the couplings. Transmission mechanisms for the FC term of four-and five-bond 19F-19F couplings are discussed in detail. Understanding the conformational preferences of PFPCs and how they are reflected by the coupling constants facilitates the assignment of 19F chemical shifts in monosubstituted PFPCs and the identification of the disubstituted products. Copyright © 2011 John Wiley & Sons, Ltd.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
John Wiley & Sons Ltd
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
19f Chemical Shifts
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19f-19f Couplings
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Conformation
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Fccp-Cmo
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Fermi Hole
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Nmr
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Paracyclophane
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Perfluoro[2.2]Paracyclophane
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Through-Space
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Otras Ciencias Químicas
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Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
19F chemical shifts, coupling constants and conformational preferences in monosubstituted perfluoroparacyclophanes
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-08-23T19:06:38Z
dc.journal.volume
49
dc.journal.number
3
dc.journal.pagination
93-105
dc.journal.pais
Reino Unido
dc.journal.ciudad
Londres
dc.description.fil
Fil: Ghiviriga, Ion. University of Florida; Estados Unidos
dc.description.fil
Fil: Zhang, Lianhao. University of Florida; Estados Unidos
dc.description.fil
Fil: Martinez, Henry. University of Florida; Estados Unidos
dc.description.fil
Fil: Contreras, Ruben Horacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Física de Buenos Aires. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Física de Buenos Aires; Argentina
dc.description.fil
Fil: Tormena, Cláudio F.. Universidade Estadual de Campinas; Brasil
dc.description.fil
Fil: Nodin, Laura. University of Florida; Estados Unidos
dc.description.fil
Fil: Dolbier Jr., William R.. University of Florida; Estados Unidos
dc.journal.title
Magnetic Resonance in Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/mrc.2713
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