Complex formation and proton transfer in the polarizable hydrogen bonds of two N,N′-dioxides + substituted phenol systems as a function of the pK<sub>a</sub>of the phenols. An FTIR study

Brzeziński, Bogumił; Schroeder, Grzegorz; Zuńdel, Georg; Keil, Thomas

doi:10.1039/p29920000819

Cited by 9 publications

(1 citation statement)

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“…In this spectrum a continuum is observed, which is particularly intense in the region 1700−700 cm -1 . Such a continuum is characteristic for strong homoconjugated hydrogen bonds with a broad flat single minimum proton potential, showing large proton polarizability. − The band at 1200 cm -1 , which is not observed in the spectrum of pure EHPO, is the bending vibration of the central proton in the homoconjugated hydrogen bonds. Hence, the structure, shown in Scheme , is present in the solution.…”

Section: Resultsmentioning

confidence: 99%

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

1997

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Complexes of tris(2-ethylhexyl) phosphate (EHPO) with HAuCl4 and its hydrates with various amounts of water were studied by FT-IR spectroscopy. In the water free solution of HAuCl4 in EHPO homoconjugated PO···H+···OP hydrogen bonds with proton polarizability are formed. We demonstrate that in the 1:1 and 1:2 mixture with water only the H5O2 + species is present and no H3O+ species is formed. In the 1:1 mixture with water in addition to the H5O2 + species, 50% homoconjugated hydrogen bonds of protonated EHPO are still present. This homoconjugated hydrogen bond, as well as the central bond in H5O2 + shows large proton polarizability, as indicated by IR continua. In the 1:3 mixture of the homoconjugated complex with water a cyclic hydrogen-bonded system with a three-minima proton potential is present. The proton polarizability of this system is the largest, as indicated by a particularly intense IR continuum. In the case of the 1:4 mixture, a cyclic hydrogen-bonded arrangement with a four-minima proton potential is present, in which the barriers between the minima are larger than in the three-minima potential.

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Section: Resultsmentioning

confidence: 99%

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

1997

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Hydrogen Bonds with Large Proton Polarizability and Proton Transfer Processes in Electrochemistry and Biology

Zuńdel¹

1999

Advances in Chemical Physics

196

126

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General and Theoretical Aspects of Phenols

Nguyen

Kryachko

Vanquickenborne

2009

Patai's Chemistry of Functional Groups

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Introduction Molecular Structure and Bonding of Phenol Structures and Properties of Substituted Phenols Energetics of some Fundamental Processes Hydrogen Bonding Abilities of Phenols Open Theoretical Problems Acknowledgements

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Complex formation and proton transfer in the polarizable hydrogen bonds of two N,N′-dioxides + substituted phenol systems as a function of the pK_aof the phenols. An FTIR study

Cited by 9 publications

References 9 publications

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

Hydrogen Bonds with Large Proton Polarizability and Proton Transfer Processes in Electrochemistry and Biology

General and Theoretical Aspects of Phenols

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Complex formation and proton transfer in the polarizable hydrogen bonds of two N,N′-dioxides + substituted phenol systems as a function of the pKaof the phenols. An FTIR study

Cited by 9 publications

References 9 publications

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

Excess Proton Hydrate Structures with Large Proton Polarizability, Screened by Tris(2-ethylhexyl) Phosphate

Hydrogen Bonds with Large Proton Polarizability and Proton Transfer Processes in Electrochemistry and Biology

General and Theoretical Aspects of Phenols

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Product

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Complex formation and proton transfer in the polarizable hydrogen bonds of two N,N′-dioxides + substituted phenol systems as a function of the pK_aof the phenols. An FTIR study