Neutron diffraction study of lithium hydrogen phthalate monohydrate: A material with two very short intramolecular O⋅⋅⋅H⋅⋅⋅O hydrogen bonds

Küppers, H.; Takusagawa, Fusao; Koetzle, Thomas F.

doi:10.1063/1.448550

Cited by 46 publications

(33 citation statements)

References 24 publications

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“…These results suggest symmetric singlewell potential with the single most probable proton position in the center of the H-bond, as illustrated in Figure 5b. 37,56 We note a recent discussion of the symmetries of strong hydrogen bonds. Perrin et al have measured 18 O isotope effects on 13 C chemical shifts of maleate, phthalate, and derivatives, 53,57 which have been interpreted in terms of an equilibrium between nonsymmetric tautomers.…”

Section: ■ Discussionmentioning

confidence: 99%

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

et al. 2012

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Ten formally symmetric anionic OHO hydrogen bonded complexes, modeling Asp/Glu amino acid side chain interactions in nonaqueous environment (CDF(3)/CDF(2)Cl solution, 200-110 K) have been studied by (1)H, (2)H, and (13)C NMR spectroscopy, i.e. intermolecularly H-bonded homoconjugated anions of acetic, chloroacetic, dichloroacetic, trifluoroacetic, trimethylacetic, and isobutyric acids, and intramolecularly H-bonded hydrogen succinate, hydrogen rac-dimethylsuccinate, hydrogen maleate, and hydrogen phthalate. In particular, primary H/D isotope effects on the hydrogen bond proton signals as well as secondary H/D isotope effects on the (13)C signals of the carboxylic groups are reported and analyzed. We demonstrate that in most of the studied systems there is a degenerate proton tautomerism between O-H···O(-) and O(-)···H-O structures which is fast in the NMR time scale. The stronger is the proton donating ability of the acid, the shorter and more symmetric are the H-bonds in each tautomer of the homoconjugate. For the maleate and phthalate anions exhibiting intramolecular hydrogen bonds, evidence for symmetric single well potentials is obtained. We propose a correlation between H/D isotope effects on carboxylic carbon chemical shifts and the proton transfer coordinate, q(1) = ½(r(OH) - r(HO)), which allows us to estimate the desired OHO hydrogen bond geometries from the observed (13)C NMR parameters, taking into account the degenerate proton tautomerism.

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Section: ■ Discussionmentioning

confidence: 99%

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

et al. 2012

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“…The data sample accidentally contains no "symmetric' three-center hydrogen bonds with geometrically similar major and minor components; therefore, the clusters of data points for major and minor components of multi-center hydrogen bonds appear to be clearly separated. In larger data samples, the apparent gap between these clusters does not exist (Jeffrey & Maluszynska, 1990: Steiner & Saenger, 1992b Takusagawa & Koetzle, 1985).…”

Section: Introductionmentioning

confidence: 99%

Lengthening of the covalent O–H bond in O–H^...O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds

Steiner¹,

Saenger²

1994

Acta Crystallogr Sect B

242

178

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“…The possible morphology of the TFP crystal of commonly growth face (001). TFP crystal cleavage faces find application as substrates in epitaxial techniques 16 . The TFP crystal was cleaving perpendicular to the (001) direction, this face and plane of crystal in this study 17 .…”

Section: Methodsmentioning

confidence: 99%

Growth, Electrical, Thermal, Optical, Physiochemical and NLO Properties of Dyes Doped Tetrafluoro Phthalate Crystals

2018

Chem Sci Trans

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A systematic study has been carried out on the growth of pure and doped tetrafluoro phthalate crystals. The lattice parameters find through powder X-ray diffraction analysis for the grown pure and doped crystals. The functional groups, stretching are found through FT-IR and FT-Raman spectroscopical analysis, optical, absorption studies through UV-Vis analysis, thermal studies under TG/DTA analysis, through Vickers test and LCR metre the microhardness and dielectric studies were also carried out for the grown pure and dyes doped crystals. The SHG efficiency of the pure and dyes doped TFP crystals were also studied using Nd:YAG Q-switched laser. The results of these investigations are discussed in this paper.

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Neutron diffraction study of lithium hydrogen phthalate monohydrate: A material with two very short intramolecular O⋅⋅⋅H⋅⋅⋅O hydrogen bonds

Cited by 46 publications

References 24 publications

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

Lengthening of the covalent O–H bond in O–H^...O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds

Growth, Electrical, Thermal, Optical, Physiochemical and NLO Properties of Dyes Doped Tetrafluoro Phthalate Crystals

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Neutron diffraction study of lithium hydrogen phthalate monohydrate: A material with two very short intramolecular O⋅⋅⋅H⋅⋅⋅O hydrogen bonds

Cited by 46 publications

References 24 publications

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on 13C NMR Chemical Shifts

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on 13C NMR Chemical Shifts

Lengthening of the covalent O–H bond in O–H...O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds

Growth, Electrical, Thermal, Optical, Physiochemical and NLO Properties of Dyes Doped Tetrafluoro Phthalate Crystals

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Product

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Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

Hydrogen Bond Geometries and Proton Tautomerism of Homoconjugated Anions of Carboxylic Acids Studied via H/D Isotope Effects on ¹³C NMR Chemical Shifts

Lengthening of the covalent O–H bond in O–H^...O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds