Publication Type Journal Article
Title Synthesis and structural studies of hexafluorophosphate-based organic salts: A combined experimental and computational analysis
Authors Marwa Belkhiria Melek Hajji Ali Mechria Tiago F. C. Cruz Clara S. B. Gomes Pedro T. Gomes Taha Guerfel Moncef Msaddek
Groups IOARC
Year 2020
Month February
Volume 1202
Abstract The neutral ligands 2-(N-2,6-dimethylphenylformimino)furan (L1), 2-(N-2,6-diisopropylphenylformimino)furan (L2), 2-(N-2,6-dimethylphenylformimino) thiophene (L3) and 2-(N-2,6-diisopropylphenylformimino)thiophene (L4) were reacted with half equivalent of bis(allyl)di-mu-mchloroodipalladium in the presence of thallium hexafluorophosphate, in dichloromethane, affording the corresponding iminium salts [(N-allyl) (L<\^>L )][PF6] (L<\^>L = L1 (1), L2 (2), L3 (3) or L4 (4)) containing one allyl group linked to the ligand through the imine nitrogen. All new organic salts 1 (C13H13NO)[PF6], 2 (C17H21NO)[PF6], 3 (C13H13NS)[PF6], and 4 (C17H21NS)[PF6] have been characterized by elemental analysis and H-1, F-19, P-31 NMR spectroscopy. Structural features in the solid state of compounds 2 and 3 were further discussed by means of X-ray crystallography, Hirshfeld surfaces HS analysis and Non-Covalent Interactions NCI-RDG topological approach. Both crystalline structures are internally stabilized via C-H center dot center dot center dot N1 H-bonds. Supramolecular assemblies are insured by non-conventional C-H center dot center dot center dot F (inter) hydrogen bonds, Cg(center dot center dot center dot)Cg (pi(center dot center dot center dot)pi) stacking and C-H(center dot center dot center dot)Cg(pi) intercontacts, as well as by van der Waals interactions and steric repulsions. Additionally, conceptual DFT global reactivity indicators, calculated at the wB97X-D/cc-pVDZ level, show that studied systems are considered strong electrophiles and marginal nucleophiles. (C) 2019 Elsevier B.V. All rights reserved.
Book Title
ISSN 0022-2860
EISSN 1872-8014
Conference Name
Bibtex ID ISI:000501486700099
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