NDLI: Lariat ethers with fluoroaryl side-arms: a study of CF⋯metal cation interaction in the complexes of <i>N</i>-(<i>o</i>-fluoroaryl)azacrown ethers

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Lariat ethers with fluoroaryl side-arms: a study of CF⋯metal cation interaction in the complexes of N-(o-fluoroaryl)azacrown ethers

Content Provider	Royal Society of Chemistry (RSC)
Author	Sergienko, Vladimir S. Churakov, Andrei V. Artamkina, Galina A. Beletskaya, Irina P. Minacheva, Lidiya Kh. Sazonov, Petr K. Oprunenko, Yuri F.
Copyright Year	2009
Abstract	New lariat ethers, N-(o-fluorophenyl)aza-15-crown-5 (F-A15C5) and N,N′-bis(o-fluorophenyl)diaza-18-crown-6 (F2-A218C6), were prepared by the N-arylation of the corresponding azacrown ethers. The interaction of the ligands with metal cations was studied in solution by 1H and 19F NMR (in acetone-d6) and UV spectroscopy (MeOH) confirming the formation of complexes of F2-A218C6 with K+, Na+, Ag+, Ba2+, Pb2+ and of F-A15C5 with Na+ and giving evidence of CF⋯metal cation interaction. Cation binding constants (β, evaluated by UV titration method), demonstrate that F-A15C5 and F2-A218C6 form more stable complexes than their fluorine-free analogs. The effect depends on the nature of the metal cation and is at a maximum for hard, singly charged cations (up to 3 logβ units for K+ complex of F2-A218C6). The X-ray structures of complexes [Pb(F2-A218C6)(H2O)](ClO4)2 (1) and [Ba(F2-A218C6)(ClO4)2] (2) reveal short Pb–F (2.805 Å) and Ba–F (2.965 Å) contacts. Complex 2 is centrosymmetric (Ci), while complex 1 has C2 symmetry with one-side coordination of o-fluorophenyl groups to Pb2+. This “one-side” coordination mode of Pb2+ is indicative of a partial localization of the Pb2+ lone pair.
Starting Page	843
Ending Page	850
Page Count	8
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	5
Journal	Dalton Transactions
DOI	10.1039/b807199c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ba RNA splicing 15-Crown-5 18-Crown-6 Fluorine-19 nuclear magnetic resonance Nuclear magnetic resonance Ultraviolet\u2013visible spectroscopy CompactFlash Ion Titration X-ray crystallography Lead Lone pair
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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