NMR and X-ray structural characterization and conformational aspects of fluorinated (5Z)-3-benzil-5-arylidenofuran-2(5H)-ones

• Published in: Journal of molecular structure Vol. 1075; pp. 53 - 62
• Main Authors: Teixeira, R.R., Barbosa, L.C.A., Kabeshov, M.A., Maltha, C.R.A., Corrêa, R.S., Doriguetto, A.C.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.10.2014
• Subjects: Crystal structure; DFT calculations; Herbicide; Nostoclide analogues; Nostoclide analogues; DFT calculations; Herbicide; Crystal structure
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2014.05.045

[Display omitted] •Structural insights of fluorinated nostoclide derivatives are presented.•Derivatives 6 and 7 crystallized in the space group P21/c.•Z stereochemistry for exocyclic double bond was confirmed via NMR and X-ray analyses.•Comparison between structural features of 6 and 7 and other nostoclide derivatives previously published are described. Herein we describe structural insights of (5Z)-3-benzyl-5-(2-fluorobenzylidene)furan-2(5H)-one (6) and (5Z)-3-benzyl-5-(pentafluorobenzylidene)furan-2(5H)-one (7), γ-alkylidenebutenolides analogues of the natural products nostoclides. Their structures were investigated by NMR spectroscopy and X-ray crystallography. The stereochemistry of the exocyclic double bond of these fluorinated compounds was determined to be Z by NMR analysis and confirmed by X-ray data. Compounds 6 and 7 crystallized in the monoclinic crystal system P21/c group. A comparison between structural features of (6) and (7) and nostoclide derivatives previously published by us is described.