Please use this identifier to cite or link to this item:
Full metadata record
DC FieldValueLanguage
dc.creatorMartins, Francisco A.-
dc.creatorSilla, Josué M.-
dc.creatorFreitas, Matheus P.-
dc.identifier.citationMARTINS, F. A.; SILLA, J. M.; FREITAS, M. P. Conformational impact of structural modifications in 2-fluorocyclohexanone. Journal of Organic Chemistry, Washington, v. 13, p. 1781-1787, 24 Ago. 2017.pt_BR
dc.description.abstract2-Haloketones are building blocks that combine physical, chemical and biological features of materials and bioactive compounds, while organic fluorine plays a fundamental role in the design of performance organic molecules. Since these features are dependent on the three-dimensional chemical structure of a molecule, simple structural modifications can affect its conformational stability and, consequently, the corresponding physicochemical/biological property of interest. In this work, structural changes in 2-fluorocyclohexanone were theoretically studied with the aim at finding intramolecular interactions that induce the conformational equilibrium towards the axial or equatorial conformer. The interactions evaluated were hydrogen bonding, hyperconjugation, electrostatic and steric effects. While the gauche effect, originated from hyperconjugative interactions, does not appear to cause some preferences for the axial conformation of organofluorine heterocycles, more classical effects indeed rule the conformational equilibrium of the compounds. Spectroscopic parameters (NMR chemical shifts and coupling constants), which can be useful to determine the stereochemistry and the interactions operating in the series of 2-fluorocyclohexanone derivatives, were also calculated.pt_BR
dc.rightsacesso abertopt_BR
dc.sourceJournal of Organic Chemistrypt_BR
dc.subjectClassical effectspt_BR
dc.subjectConformational analysispt_BR
dc.subjectEfeitos clássicospt_BR
dc.subjectAnálise conformacionalpt_BR
dc.titleConformational impact of structural modifications in 2-fluorocyclohexanonept_BR
Appears in Collections:DQI - Artigos publicados em periódicos

Files in This Item:
File Description SizeFormat 
ARTIGO_Conformational impact of structural modifications in 2-fluorocyclohexanone.pdf180,77 kBAdobe PDFView/Open

This item is licensed under a Creative Commons License Creative Commons