NDLI: Hydrogen Bonding and Solvent Effects on Complexation of Alkali Metal Cations by Lower Rim Calix[4]arene Tetra(O-[N-acetyl-D-phenylglycine methyl ester]) Derivative

Content Provider	Springer Nature Link
Author	Tomišić, Vladislav Galić, Nives Bertoša, Branimir Frkanec, Leo Simeon, Vladimir Žinić, Mladen
Copyright Year	2005
Abstract	Complexation of alkali metal cations with 5,11,17,23-tetra-tert-butyl-26,28,25,27-tetrakis(O-methyl-D-α-phenylglycylcarbonylmethoxy)calix[4]arene (L) was studied by means of spectrophotometric, conductometric and potentiometric titrations at 25 °C. The solvent effect on the binding ability of L was examined by using two solvents with different affinities for hydrogen bonding, viz. methanol and acetonitrile. Despite the presence of intramolecular NH···O=C hydrogen bonds in L, which need to be disrupted to allow metal ion binding, this calix[4]arene amino acid derivative was shown to be an efficient binder for smaller Li$^{+}$ and Na$^{+}$ cations in acetonitrile (lg K $_{LiL }$ > 5, lg K $_{NaL }$ = 7.66), moderately efficient for K$^{+}$ (lg K $_{KL }$ = 4.62), whereas larger Rb$^{+}$ and Cs$^{+}$ did not fit in its hydrophilic cavity. The complex stabilities in methanol were significantly lower (lg K $_{NaL }$ = 4.45, lg K $_{KL }$ = 2.48). That could be explained by different solvation of the cations and by competition between the cations and methanol molecules (via hydrogen bonds) for amide carbonyl oxygens. The influence of cation solvation on complex stability was most pronounced in the case of Li$^{+}$ for which, contrary to the quite stable LiL $^{+}$ complex in acetonitrile, no complexation was observed in methanol under the conditions used.
Starting Page	263
Ending Page	268
Page Count	6
File Format	PDF
ISSN	09230750
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	53
Issue Number	3-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2005-01-01
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	alkali cations calixarenes complexation hydrogen bonds solvent effects stability constants Organic Chemistry Food Science Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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