NDLI: Symmetrization of Cationic Hydrogen Bridges of Protonated Sponges Induced by Solvent and Counteranion Interactions as Revealed by NMR Spectroscopy

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Symmetrization of Cationic Hydrogen Bridges of Protonated Sponges Induced by Solvent and Counteranion Interactions as Revealed by NMR Spectroscopy

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Elguero, José Denisov, Gleb S. Tolstoy, Peter M. Pietrzak, Mariusz Shenderovich, Ilya G. Kong, Shushu Limbach, Hans-heinrich López, Concepción Claramunt, Rosa María Wehling, Jens P.
Description	Author Affiliation: Pietrzak M ( Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, Berlin, Germany.)
Abstract	The properties of the intramolecular hydrogen bonds of doubly $^{15}N-labeled$ protonated sponges of the 1,8-bis(dimethylamino)naphthalene $(DMANH^{+})$ type have been studied as a function of the solvent, counteranion, and temperature using low-temperature NMR spectroscopy. Information about the hydrogen-bond symmetries was obtained by the analysis of the chemical shifts $δ_{H}$ and $δ_{N}$ and the scalar coupling constants J(N,N), J(N,H), J(H,N) of the $^{15}NH^{15}N$ hydrogen bonds. Whereas the individual couplings J(N,H) and J(H,N) were averaged by a fast intramolecular proton tautomerism between two forms, it is shown that the sum \|J(N,H)+J(H,N)\| generally represents a measure of the hydrogen-bond strength in a similar way to $δ_{H}$ and J(N,N). The NMR spectroscopic parameters of $DMANH^{+}$ and of $4-nitro-DMANH^{+}$ are independent of the anion in the case of $CD_{3}CN,$ which indicates ion-pair dissociation in this solvent. By contrast, studies using $CD_{2}Cl_{2},$ $[D_{8}]toluene$ as well as the freon mixture $CDF_{3}/CDF_{2}Cl,$ which is liquid down to 100 K, revealed an influence of temperature and of the counteranions. Whereas a small counteranion such as trifluoroacetate perturbed the hydrogen bond, the large noncoordinating anion tetrakis[3,5-bis(trifluoromethyl)phenyl]borate $B[\{C_{6}H_{3}(CF_{3})_{2}\}_{4}]^{−}$ $(BARF^{−}),$ which exhibits a delocalized charge, made the hydrogen bond more symmetric. Lowering the temperature led to a similar symmetrization, an effect that is discussed in terms of solvent ordering at low temperature and differential solvent order/disorder at high temperatures. By contrast, toluene molecules that are ordered around the cation led to typical high-field shifts of the hydrogen-bonded proton as well as of those bound to carbon, an effect that is absent in the case of neutral NHN chelates.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	5
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-02-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	1-Naphthylamine Analogs & Derivatives Cations Chemistry Hydrogen Crystallography, X-Ray Hydrogen Bonding Magnetic Resonance Spectroscopy Models, Molecular Porosity Protons Solvents Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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