Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalyst

Türkmen, Yunus E.

doi:10.3906/kim-1806-68

Cited by 11 publications

(13 citation statements)

References 22 publications

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“…13, 154.45, 136.71, 127.70, 125.58, 121.84, 118.84, 115.04, 110.40, 103.86, and 56.08. These NMR data are in good agreement with those reported in Emre (2018). In addition, the mass spectrum of this compound showed an m/z of 175.0759, with a predicted chemical formula of C 11 H 11 O 2 .…”

Section: Isolation and Identification Of The Active Compoundssupporting

confidence: 90%

“…1 Hand 13 C-NMR spectra were recorded at 300 and 75 MHz, respectively, using a Bruker AVANCE 300 spectrometer with CDCl 3 as an internal standard. The obtained NMR data was compared to those found in the report of Emre (2018). A mass spectrum of the isolated compound was obtained using a Bruker MicroTOF LC mass spectrometer (Bruker, United Kingdom).…”

Section: Isolation Of Antifungal Compound From the Endophytic Fungus mentioning

confidence: 99%

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Antifungal activity of 8-methoxynaphthalen-1-ol isolated from the endophytic fungus Diatrype palmicola MFLUCC 17-0313 against the plant pathogenic fungus Athelia rolfsii on tomatoes

Tanapichatsakul

Pansanit

Monggoot³

et al. 2020

PeerJ

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Thirty-four endophytic fungal isolates were obtained from the leaves of the medicinal plant Polyscias fruticosa, and their antagonistic activities against the growth of the common tomatoes plant pathogenic fungus Athelia rolfsii were initially screened using a dual culture assay. The endophytic fungus MFLUCC 17-0313, which was later molecularly identified as Diatrype palmicola, displayed the highest inhibition percentage (49.98%) in comparison to the others. This fungus was then chosen for further evaluation. Its culture broth and mycelia from a 10 L scale were separated and extracted using ethyl acetate, methanol, and hexane. Each extract was tested for antifungal activity against the same pathogen using a disc diffusion assay. Only the crude hexane extract of fungal mycelium showed antifungal activity. The hexane extract was fractioned using sephadex gel filtration chromatography and each fraction was tested for antifungal activity until the one with the highest inhibition percentage was obtained. The bioactive compound was identified as 8-methoxynaphthalen-1-ol using nuclear magnetic resonance spectroscopy and mass spectrometry. The minimum inhibition concentration of 8-methoxynaphthalen-1-ol was demonstrated at 250 µg/mL against the selected pathogen. Using the leaf assay, the solution of 8-methoxynapthalen-1-ol was tested for phytotoxic activity against A. rolfsii and was found to have no phytotoxic effects. These results showed that 8-methoxynaphthalen-1-ol has the potential for controlling the growth of A. rolfsii, the cause of Southern blight disease on tomatoes. This study may provide the foundation for future use of this compound as a biofungicide.

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Section: Isolation and Identification Of The Active Compoundssupporting

confidence: 90%

Section: Isolation Of Antifungal Compound From the Endophytic Fungus mentioning

confidence: 99%

Antifungal activity of 8-methoxynaphthalen-1-ol isolated from the endophytic fungus Diatrype palmicola MFLUCC 17-0313 against the plant pathogenic fungus Athelia rolfsii on tomatoes

Tanapichatsakul

Pansanit

Monggoot³

et al. 2020

PeerJ

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“…The conformational analysis of 1,8-DHN (8) in solution phase was studied by 1 H-NMR spectroscopy in CDCl 3 and d 6 -DMSO solvents ( Figure 5). [20] A thorough analysis was reported by M. H. Abraham, R. J. Abraham and co-workers on the 1 H-NMR spectra of various HB donors in CDCl 3 and d 6 -DMSO, and it was pointed out that the HB donating ability correlates well with the difference in chemical shifts in these two solvents. [23] When the 1 H-NMR spectra of 1-naphthol (10) were recorded in CDCl 3 and d 6 -DMSO (0.05 M), the chemical shift of the À OH hydrogen was observed to be 5.28 and 10.08 ppm, respectively (Figures 5a and 5b).…”

Section: Conformational Analysismentioning

confidence: 99%

“…As described in our initial report, the chemical shift changes (Δδ) in the 31 P-NMR spectra of Ph 3 PO in CDCl 3 upon complexation to naphthol derivatives 8, 9 and 10 were determined first. [20] While a Δδ value of 3.24 ppm was observed for a 1 : 1 mixture of diol 8 and Ph 3 PO in CDCl 3 , using 2 equivalents of 1-naphthol (10) induced a lower chemical shift change (2.33 ppm) indicating higher HB donating ability of diol 8 compared to 10 (Table 1). [27] As expected from the conformational analysis studies described above, 8-methoxy-1-naphthol (9) does not act as a strong HB donor, and led to almost no change in the 31 P-NMR spectrum when mixed with Ph 3 PO in a 1 : 2 ratio (Δδ = À 0.02 ppm).…”

Section: Binding Studiesmentioning

confidence: 99%

“…Our preliminary results on the use of NMR spectroscopy for the evaluation of the HB donating ability of diol 8 were recently reported. [20] Herein, we are reporting a full account of our studies on the polarizationenhanced hydrogen bonding in 1,8-DHN (8). In the first section, we investigated the conformation of 8, and the nature of its intra-and intermolecular HBs by X-ray crystallography, NMR spectroscopy, and by computational methods.…”

Section: Introductionmentioning

confidence: 99%

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Polarization‐Enhanced Hydrogen Bonding in 1,8‐Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis

et al. 2020

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In this article, the presence and effects of polarizationenhanced hydrogen bonding in 1,8-dihydroxynaphthalene (1,8-DHN) were investigated in detail through a series of experimental and computational studies. First, the conformation of 1,8-DHN, and its ability to make intra-and intermolecular hydrogen bonds were investigated in solid state by X-ray crystallography, in solution by NMR spectroscopy, and computationally by density functional theory. Second, equilibrium binding constants, which were determined by 31 P-NMR titration studies, demonstrated stronger complexation of Ph 3 PO with 1,8-DHN compared to mono-naphthol derivatives 8-methoxy-1naphthol and 1-naphthol. In the final section, 1,8-DHN was observed to be an effective catalyst for the Friedel-Crafts-type addition reaction of indoles to β-nitrostyrenes, and a rationale for this catalytic activity was provided via computational studies. All the findings described in this work support the enhanced hydrogen bond donating ability of 1,8-DHN due to polarization caused by the six-membered intramolecular hydrogen bond present in its structure.

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Cooperativity and topological hydrogen bonding in aromatic diol complexes

Rosenberg,

Lomas

2023

J of Physical Organic Chem

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Complexes of three aromatic diols, catechol, naphthalene‐1,8‐diol, and fluorene‐4,5‐diol, with a series of hydrogen bond acceptors (HBAs) that have oxygen, nitrogen, and sulfur acceptor atoms, have been studied by density functional theory (DFT) at the B3LYP/6‐311+G(d,p) level. Binding energies, geometries, infrared spectroscopic (IR) frequencies, nuclear magnetic resonance (NMR) shifts, and measures of the electron density distribution from the Quantum Theory of Atoms in Molecules (QTAIM) are evaluated and compared with data for the corresponding monohydroxy compounds (monols), phenol, naphth‐1‐ol, and fluorene‐4‐ol, in order to assess the importance of cooperativity between intramolecular and intermolecular hydrogen bonding. All measures for all complexes show positive cooperativity whereby both the intermolecular and intramolecular hydrogen bonds are strengthened upon complexation. Cooperativity is weak for catechol and strong for the other two diols and, for all diols, increases with the hydrogen bond basicity of the acceptor. Correlations of IR and NMR metrics against binding energies for a single HBA and all six monols and diols are excellent, but attempts to correlate the same metrics for all HBAs and a single donor are frustrated by differences in intermolecular hydrogen bonding, depending notably on the identity of the acceptor atom in the HBA. Atom–atom interaction energies, calculated by the Interacting Quantum Atoms approach, are used to discuss the covalency of both types of hydrogen bond.

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Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalyst

Cited by 11 publications

References 22 publications

Antifungal activity of 8-methoxynaphthalen-1-ol isolated from the endophytic fungus Diatrype palmicola MFLUCC 17-0313 against the plant pathogenic fungus Athelia rolfsii on tomatoes

Antifungal activity of 8-methoxynaphthalen-1-ol isolated from the endophytic fungus Diatrype palmicola MFLUCC 17-0313 against the plant pathogenic fungus Athelia rolfsii on tomatoes

Polarization‐Enhanced Hydrogen Bonding in 1,8‐Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis

Cooperativity and topological hydrogen bonding in aromatic diol complexes

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