Analysis of isotropic chemical shift data from high-resolution solid-state NMR studies of hydrogen-bonded organic compounds

Etter, Margaret C.; Reutzel, Susan M.; Vojta, Gail M.

doi:10.1016/0022-2860(90)80138-a

Cited by 13 publications

(4 citation statements)

References 24 publications

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“…For 1, Vila et al previously reported 13 C chemical shifts for C1 and C3 of 182.9 and 188.2 ppm, respectively, 22 whereas Etter et al reported 182.3 and 187.6 ppm. 21 Similar to the 13 C NMR observations, the two oxygen atoms in each of the O•••H•••O LBHBs in 1 and 2 also display different chemical shifts. As seen from Figure 1, the 17 O MAS spectra contain two signals each displaying a characteristic line shape arising from the second-order quadrupole interaction.…”

Section: Resultssupporting

confidence: 63%

“…reported a 1 H chemical shift of 18.1 ppm. , In the 13 C CP/MAS spectra of 1 and 2 , shown in Figure , the most interesting feature is that the C1 and C3 atoms display different 13 C chemical shifts: 182.7 and 188.0 ppm in 1 ; 182.7 and 187.4 ppm in 2 . For 1 , Vila et al previously reported 13 C chemical shifts for C1 and C3 of 182.9 and 188.2 ppm, respectively, whereas Etter et al reported 182.3 and 187.6 ppm …”

Section: Results and Discussionmentioning

confidence: 98%

“…Dibenzoylmethane was chosen because it has been previously studied by both neutron and X-ray diffraction as well as by solid-state 1 H and 13 C NMR. − An early neutron diffraction study of dibenzoylmethane suggests that the O 1 ···O 2 separation is 2.463 (4) Å and that the enolic H atom is asymmetrically placed between the two O atoms, with the difference in O–H bond lengths being 0.199 (17) Å. In a more recent combined X-ray/neutron diffraction study of dibenzoylmethane, Wilson and co-workers highlighted the complementary nature of the two diffraction techniques, one being sensitive to the electronic density and the other to the nuclear density.…”

Section: Introductionmentioning

confidence: 99%

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Proton Probability Distribution in the O···H···O Low-Barrier Hydrogen Bond: A Combined Solid-State NMR and Quantum Chemical Computational Study of Dibenzoylmethane and Curcumin

et al. 2016

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We report a combined solid-state (H, H,C, O) NMR and plane-wave density functional theory (DFT) computational study of the O···H···O low-barrier hydrogen bonds (LBHBs) in two 1,3-diketone compounds: dibenzoylmethane (1) and curcumin (2). In the solid state, both 1 and 2 exist in the cis-keto-enol tautomeric form, each exhibiting an intramolecular LBHB with a short O···O distance (2.435 Å in 1 and 2.455 Å in 2). Whereas numerous experimental (structural and spectroscopic) and computational studies have been reported for the enol isomers of 1,3-diketones, a unified picture about the proton location within an LBHB is still lacking. This work reports for the first time the solid-stateO NMR data for the O···H···O LBHBs in 1,3-diketones. The central conclusion of this work is that detailed information about the probability density distribution of the proton (nuclear zero-point motion) across an LBHB can be obtained from a combination of solid-state NMR and plane-wave DFT computations (both NMR parameter calculations and ab initio molecular dynamics simulations). We propose that the precise proton probability distribution across an LBHB should provide a common basis on which different and sometimes seemingly contradicting experimental results obtained from complementary techniques, such as X-ray diffraction, neutron diffraction, and solid-state NMR, can be reconciled.

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Section: Resultssupporting

confidence: 63%

Section: Results and Discussionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Proton Probability Distribution in the O···H···O Low-Barrier Hydrogen Bond: A Combined Solid-State NMR and Quantum Chemical Computational Study of Dibenzoylmethane and Curcumin

et al. 2016

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“…Clues about the structure of acid−soaps have come from extrapolation to single-crystal data collected for fatty acids, − short-chain acid−soap crystals such as sodium hydrogen diacetate, and potassium hydrogen phenylacetate and to a survey of existing single-crystal data of similar compounds . Structural details are crucial to understanding the “anomalous” infrared − and NMR ,, data on powder acid−soap crystals, which show that acid−soap crystals maintain some carboxylic acid-like character and some carboxylate anion-like character, which are quantitatively different from the character of either the parent fatty acid or the sodium carboxylate. The present combined crystallographic and molecular dynamics (MD) simulation study has been undertaken to provide the first structural description of these long chain length acid−soaps that allows for detailed understanding of the spectroscopy and solid-state chemistry of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular Interactions and the Structure of Fatty Acid−Soap Crystals

et al. 2000

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Single crystals of NaHP2 (sodium hydrogen dipalmitate) have been prepared from mixtures of NaP (sodium palmitate) and HP (palmitic acid) in ethanol. The phase compound crystallizes in the P21/a space group, with a = 9.906 Å, b = 7.163 Å, c = 45.580 Å, β = 92.78°, and 4 molecules per unit cell. The arrangement of the headgroups is unique among known soap and fatty acid structures by accommodating both hydrogen bonding and electrostatic interactions. Carboxylate and acid-like pairs couple perpendicular to the bilayer to accommodate a “short” hydrogen bond, and the sodium is shared among laterally adjacent carboxylate anions to create a pseudo-six-member ring, which adds to the crystal stability. Molecular dynamic (MD) simulations establish a set of interaction parameters to describe the structure and energetics of acid−carboxylate bonds, which accounts for the solid-state miscibility of HP and NaP. Infrared data, collected by ATR-FTIR on very pure, powdered NaH2P3, Na2H3P5, and NaHP2 acid−soap standards reveal peculiar changes in the carbonyl and hydroxyl spectral regions. These spectra were analyzed on the basis of crystal structure and MD simulation data.

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Hydrogen Bonding

Becker

2007

Encyclopedia of Magnetic Resonance

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Analysis of isotropic chemical shift data from high-resolution solid-state NMR studies of hydrogen-bonded organic compounds

Cited by 13 publications

References 24 publications

Proton Probability Distribution in the O···H···O Low-Barrier Hydrogen Bond: A Combined Solid-State NMR and Quantum Chemical Computational Study of Dibenzoylmethane and Curcumin

Proton Probability Distribution in the O···H···O Low-Barrier Hydrogen Bond: A Combined Solid-State NMR and Quantum Chemical Computational Study of Dibenzoylmethane and Curcumin

Intermolecular Interactions and the Structure of Fatty Acid−Soap Crystals

Hydrogen Bonding

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