Carbonyl Oxygen Atom Research Articles

Towards high-performance nonlinear optical materials through embedding a D-A system into β-ketoenamine-linked COFs.

Two covalent organic framework (COF) films supported by a glass substrate were obtained by solvothermal reaction of an electron donor with electron acceptor 1,3,5-triformylbenzene (TF) or 2,4,6-triformylphloroglucinol (TFP), respectively. The TFP-BD film exhibits a nonlinear absorption coefficient of -3.01 × 105 cm GW-1. The TFP-BD film can aggregate electrons around the connected monomer through the D-A effect due to its highly polar and electronegative carbonyl oxygen atoms, thereby modulating the electronic structure of the COFs. This work provides a novel approach for the structural modulation of optical materials with strong nonlinearity.

Regulation of Ion Permeation of the KcsA Channel by Applied Midinfrared Field.

Ion transport molecules are involved in many physiological and pathological processes and are considered potential targets for cancer treatment. In the large family of ion transport molecules, potassium (K) ion channels, as surface-expressed proteins, show the highest variability and most frequent expression changes in many tumor types. The key to exploring the permeation of K+ through potassium channels lies in the conserved sequence TVGYG, which is common in the selectivity filter (SF) region of all potassium channels. We found that the K+ flux significantly increased with the help of a specific frequency terahertz electromagnetic wave (51.87 THz) in the KcsA channel using a molecular dynamics combined model through the combined simulation of the constant electric field method and ion imbalance method. This frequency has the strongest absorption peak in the infrared spectrum of -C=O groups in the SF region. With the applied electric field of 51.87 THz, the Y78 residue at the S1 site of the SF has a smaller vibration amplitude and a more stable structure, which enables the K+ to bind closely with the carbonyl oxygen atoms in the SF and realize ion conduction in a more efficient direct Coulomb knock-on.

Trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic Acid: Remarkable Host Selectivities in the Presence of Mixtures of Anisole and Bromoanisole Isomers

In this work, trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (DED), a host compound that formed complexes with anisole (ANI), 2-bromoanisole (2-BA), and 4-bromoanisole (4-BA), was revealed to possess a remarkable affinity (93.1–98.6%) for 4-BA when recrystallized from any mixtures containing this guest species, be these binary (ANI/4-BA, 2-BA/4-BA, or 3-BA/4-BA), ternary (ANI/2-BA/4-BA, ANI/3-BA/4-BA, or 2-BA/3-BA/4-BA), or quaternary (ANI/2-BA/3-BA/4-BA) in nature. Furthermore, this striking host selectivity persisted even in binary solutions containing low concentrations of 4-BA (18–25%); near-complete selectivities in favor of 4-BA were observed here too. Single crystal X-ray diffraction analyses showed that the favored guest species, 4-BA, was the only one to experience short intermolecular contacts, through its phenyl ring, with the host molecule’s carbonyl oxygen atom and the host hydrogen atom on the carbon bearing the second carboxylic acid group. Furthermore, ANI and 2-BA were accommodated in wide open channels, while the guest accommodation type for 4-BA was significantly more constricted. Thermal analyses confirmed that 2(DED)·3(ANI) and DED·2-BA, having the disfavored guests in open channels, were unstable at room temperature, while the preferred guest species, 4-BA, in its decidedly constricted channels, was only released at significantly higher temperatures (116.8 °C). Therefore, by employing host–guest chemistry strategies, DED has the ability to purify and separate any of these 4-BA-containing mixtures, a distinct advantage over fractional distillations which are cumbersome owing to physical property similarities of 2-, 3-, and 4-BA.

Segmental Motion Adjustment of the Polycarbonate Electrolyte for Lithium-Metal Batteries.

Carbonyl oxygen atoms are the primary active sites to solvate Li salts that provide a migration site for Li ions conducting in a polycarbonate-based polymer electrolyte. We here exploit the conductivity of the polycarbonate electrolyte by tuning the segmental motion of the structural unit with carbonyl oxygen atoms, while its correlation to the mechanical and electrochemical stability of the electrolyte is also discussed. Two linear alkenyl carbonate monomers are designed by molecular engineering to combine methyl acrylate (MA) and the commonly used ethylene carbonate (EC), w/o dimethyl carbonate (DMC) in the structure. The integration of the DMC structural unit in the side chain of the in situ constructed polymer (p-MDE) releases the free motion of the terminal EC units, which leads to a lower glass-transition temperature and higher ionic conductivity. While pure polycarbonates are normally fragile with high Young's modulus, such a prolonged side chain also manipulates the flexibility of the polymer to provide a mechanical stable interface for Li-metal anode. Stable long-term cycling performance is achieved at room temperature for both LiFePO4 and LiCoO2 electrodes based on the p-MDE electrolyte incorporated with a solid plasticizer.

ANTIBACTERIAL AND ANTIFUNGAL PROPERTIES OF Zn COMPLEXES WITH N’-ACIL-SALICYLICHYDRAZIDES

The antibacterial (Pseudomonas aeruginosa and Mycobacterium phlei) and antifungal (Aspergillus niger, Penicillium Chrysogenium, Penicillium chrosegenum, Cladosporium resinae) properties of Zn complexes with the potentially tridentate (carbonyl and hydroxyl oxygen atoms of the salicylic fragment and nitrogen atom of the amide group) N'-phthalimido-salicylamide ligand and potentially heptadentate (carbonyl and hydroxyl oxygen atoms of the salicylic fragment, two nitrogen atoms of the hydrazide fragment and two oxygen atoms of the carbonyl and carboxyl groups of the maleic fragment) N'-maleoyl-salicylhydrazide ligand were studied. The antibacterial and antifungal efficacy of the samples was determined by the zonal diffusion method according to GOST 9.085-78. Meat-peptone agar (MPA) was used for growing bacterial cultures, and wort-agar (WA) was used for fungi. These studies have shown that both ligands do not show antibacterial action, but show antifungal action. Zinc complexes of these ligands exhibit both antibacterial and antifungal effects. The antimicrobial action of the complexes is much higher than that of the ligands themselves, and this action increases with an increase in the concentration of complex compounds in solution. The antioxidant effect of the compounds H2L, H4L, (H3L)2Zn, (HL)2Zn synthesized by us was studied in cumene oxidation reactions - cumene autoxidation and reactions with cumene peroxide. Establishing the mechanism of action as an inhibitor or antioxidant that prevents oxidation as a result of the presence of the above compounds was studied in the study of cumene autoxidation

Organotellurium(IV) complexes of N-methylisatin-o-aminothiophenol Schiff base: Preparation, characterization, DFT, molecular docking studies, antimicrobial and antioxidant activity

The reactions of organotellurium(IV) chlorides (RTeCl3 and R2TeCl2) with Schiff base(NMeIATP) derived by condensation of N-methylisatin with 2-aminothiophenol results in the formation of new organotellurium(IV) complexes (4a-4f) of type RTeCl2.NMeIATP and R2TeCl.NMeIATP (where R = 4-Methoxyaryl, 4-Hydroxyaryl and 3-Methy-4-hydroxyaryl; aryl = phenyl). These complexes were characterized by different experimental and spectroscopic techniques like elemental analyses, molar conductance, SEM analysis, FT-IR, DFT calculations, powder X-ray diffraction, mass spectrometry, 1H NMR, 13C NMR, UV–Vis and Thermogravimetric analysis. These spectroscopic studies revealed that ligand acted as monobasic tridentate ligand coordinated with tellurium metal through Carbonyl oxygen, azomethine nitrogen and sulphur atom from the 2-aminothiophenol ring. The molecular geometries of NMeIATP and its organotellurium(IV) complexes(4a-4f) were optimized and quantum mechanical parameters were calculated by using DFT/B3LYP basis sets in Guassian09 program. Based on the spectral results, suitable geometries of the complexes are purposed. Molecular docking studies were carried out to determine the binding energy between NMeIATP and complexes with receptor proteins: S. aureus (3ty7), B. subtilis (5h67) and E. coli (3t88). Antioxidant activity of NMeIATP and organotellurium(IV) complexes were evaluated by DPPH assay. The radical scavenging activity(IC50 value) of complex 4a (IC50 = 59.08 μg/ml) was found to be greater than other compounds. NMeIATP and organotellurium(IV) complexes were tested against different bacteria and fungi. MIC values show that complexes possess better antimicrobial activity than Schiff base (NMeIATP).

Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones

A non-metal catalyzed deamination of propargylamines was achieved by using DBU as the catalyst and water as the carbonyl oxygen atom source. The role of DBU was found to promote the alkyne-allene isomerization process, followed by the hydrolysis to access a wide range of chalcones in good to excellent yields. This newly developed strategy features metal-free, good functional group compatibility, mild conditions, and operational simplicity.

An interesting case of symmetry breaking in the absence of symmetry: the bicarbonate radical (HCO3)

As part of a computational study of the thermochemical properties of systems related to carbonic acid (HCO), an interesting phenomenon was observed in the bicarbonate radical (HCO). This species belongs to the class of formoxyl radicals, but lacks the geometric symmetry of the more heavily-studied and prototypical HCO and FCO molecules. However, it is not immune from the problems that those molecules present to electronic structure calculations. Specifically, at geometries in the vicinity of the equilibrium structure, three solutions to the unrestricted Hartree-Fock equations can be found: two in which the unpaired spin is largely localized onto one of the (inequivalent) carbonyl oxygen atoms, and one in which the spin is delocalized. While all three of these reference functions comprise orbitals that transform as pure irreducible representations of the point group, the two localized choices qualitatively correspond to the symmetry-broken solution of the formoxyl species and the delocalized solution qualitatively corresponds to the symmetry-preserving (but orbitally unstable) solution. The three solutions are described in this work, as well as the corresponding ambiguities that result in the thermochemical characterization of this species.

Die Kristallstrukturen der Komplexe von 2,6-Dimethyl-γ-Pyron mit BF3, CuCl2 und HgCl2

Abstract The crystal structures of the complexes of 2,6-dimethyl-4H-pyran-4-one (DMP) with BF3, CuCl2 and HgCl2 have been investigated. In all three case, the site of coordination is to the carbonyl (exocyclic) oxygen atom. DMP·BF3 (I) crystallizes with the monoclinic space group C2/c and the lattice parameters a = 1023.98(5), b = 1465.74(7), c = 1169.03(6) pm, β = 101.347(2)°. In this molecular structure the non-connected molecules are arranged in layers, which spread out parallel to the ab plane. Starting from planar BF3, this molecule is converted by coordination to a tetrahedral entity −OBF3. DMP·CuCl2 (II) belongs to the orthorhombic space group Pnma with a = 1952.43(9), b = 670.84(3), c = 1362.30(6) pm and two different Cu2+ cations. All atoms except the Cl− anions and two atoms of the −CH3 groups reside in mirror planes. The coordination around both Cu2+ cations is square pyramidal −OCuCl4 with the oxygen atom at the apex. The bases are planar and connected via trans-oriented edges to form a strand, running parallel to the b axis. DMP·HgCl2 (III) crystallizes with the space group P21/n and the lattice parameters a = 767.59(4), b = 1970.32(9), c = 1374.41(6) pm, β = 98.257(2)°. Its monoclinic structure is a distorted version of the orthorhombic copper(II) complex structure. The reason is the preference of Hg2+ for the short linear arrangement Cl−Hg−Cl. It is demonstrated, that the crystal structure of DMP·HgCl2 belongs to a translationsgleiche subgroup of the DMP·CuCl2 structure.

Construction of imide-functionalized aromatic conjugation tetracarboxylate frameworks and adsorption behavior for iodine and selective cationic dyes

Metal-organic frameworks (MOFs) show great potential in environmental contaminants removal owing to their outstanding pore properties and tunable chemical performance. Two new imide-functionalized aromatic conjugation tetracarboxylate frameworks: [Cd4(BDCPPI)2(DMF)2(H2O)3]·2DMF·8H2O (1) and [Zn4(BDCPPI)2(DMF)6]·3DMF·4H2O (2) were designed and synthesized under solvothermal conditions. Due to the micropore size and aromatic conjugation properties with the 3D network structures, complexes 1 and 2 have abundant active sites, resulting in strong iodine capture and dye adsorption capacity. The excellent iodine capture ability on complexes 1 and 2 might due to the interaction of iodine with the carbonyl oxygen atom (I⋯O) and the benzene ring (I···π). The materials were charge and size selective for the adsorption of dyes, and the presence of abundant imide-functionalized groups in the channels can form hydrogen-bonding interactions with dye molecules to promote their adsorption properties. In addition, the high I2 adsorption and release capacity of complexes 1 and 2 indicate their wide application prospects in nuclear waste management. Therefore, the as-synthesized MOFs can be used as potential multifunctional adsorbents for further removal of organic dyes and iodine from wastewater.

Structure and free volume of fluorine-containing polyetherimides with pendant di-tert-butyl groups investigated by molecular dynamics simulation

The study is focused on the investigation of structural properties of 5 polyetherimides (PEIs) containing 1,4-bis-[{2′-trifluoromethyl 4′-(4″-aminophenyl)phenoxy}]-2,5-di-tert-butylbenzene diamine monomer (FMTBDA) and 5 different dianhydride monomers (PMDA, BTDA, ODPA, 6FDA, and BPADA) using molecular dynamics simulations. 32 independent models were built for each polymer. Densities calculated for the modeled samples were compared with the experimental ones, giving difference of up to 6%. Accessible free volume (AFV) distribution was evaluated for the investigated polymers. It was shown that AFV for all the probe sizes decreased in a row: PMDA > BTDA∼6FDA > ODPA > BPADA, which is in line with the experimental gas transport parameters shown previously. Bimodal AFV distribution was demonstrated. Specific surface area (SSA) was calculated for the models of polymers, and fragments composing the inner surface of the free volume were determined. Analysis of the elements of the free volume surface has shown that sp 3 carbon (С sp3 ), carbonyl oxygen (O C=O ), and fluorine (F) atoms tend to form free volume elements, while imide nitrogen (N imide ) and ether oxygen (O ether ) tend to compose polymer bulk. • Accessible cavities distribution shows bimodal behavior for FMTBDA PEIs. • C Sp3 , carbonyl oxygen and fluorine atoms tend to form free volume elements. • Imide nitrogen and ether oxygen tend to compose FMTBDA PEIs polymer bulk. • ∼50% of H 2 AFV in FMTBDA PEIs is also accessible to molecules larger than O 2 .

Metabolic Disorder Enhances Oxidative Stress after Exposure to Aromatic Components of Fine Particulate Matter

Metabolic disorder can exacerbate oxidative damage following exposure to fine particulate matter (PM2.5), but the role of chemical composition in this process remains unclear. This study comprehensively assessed the oxidative stress effect from the synergy of metabolic disorder and the organic components in PM2.5 as well as their molecular features. We high-throughput characterized 942 PM2.5 chemicals from an elderly urban population exposure and found the association between oxidative stress markers of exhaled nitric oxide (eNO) and urinary malondialdehyde (MDA) and 330 and 32 compounds, respectively, was enhanced by metabolic disorder. Most of these compounds were aromatics, including PAHs and their functionalized and oxidized products. The integrated explanatory random forest approach incorporating source tracers showed that primary aromatics arising from combustion with a high unsaturation degree, high logKOW, and low volatility were responsible for the increased eNO levels in participants with metabolic disorder, while compounds formed through atmospheric oxidation reactions with high numbers of carbonyl groups and oxygen atoms and relatively low logKOW were associated with elevated MDA in disordered individuals. This study provides the first evidence that metabolic disorder exacerbates oxidative stress after exposure to specific PM2.5 components, which could in turn exacerbate chronic diseases in the elderly population.

Density functional theory studies on molecular geometry, spectroscopy, HOMO-LUMO and reactivity descriptors of titanium(IV) and oxidozirconium(IV) complexes of phenylacetohydroxamic acid.

The molecular geometry of new titanium(IV) and oxidozirconium(IV) phenylacetohydroxamate complexes [TiCl2 (L1)2 ] (I) and [ZrO(L1)2 ] (II) (where L1=Potassium phenylacetohydroxamate=C6 H5 CH2 CONHOK) computed by B3LYP/6-311++G(d,p) method has shown these to be distorted octahedral and square pyramidal, respectively. A comparison of computed characteristic bond lengths (CO, CN, and NO) of complexes with that of free ligand has shown chelation through carbonyl and hydroxamic oxygen atoms (O, O coordination). The TiO/ZrO bond lengths in complexes are suggestive of weak coordination through (carbonyl CO) and strong covalent (hydroxamic NO) bonding of the ligand. The magnitude of ClTiCl bond angle involving two chloride atoms is suggestive of cis-conformation at titanium metal in (I). The thermodynamic parameters Gibbs free energy, enthalpy, entropy, nuclear internal energy, constant volume heat capacity, and internal energy of ligand and complexes have been computed. From the energies of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), the global reactivity descriptors such as ionization potential (IP), electron affinity (EA), chemical potential (μ), hardness (η), softness (S), electronegativity (χ), electrophilicity index (ω), and dipole moment have been calculated. The computed vibrational frequencies, 1 H and 13 C NMR spectra have substantiated the molecular structure of complexes. The thermal behavior of complexes has been studied by thermogravimetric techniques (TGA, DTG, and DTA) in N2 atmosphere has shown complexes are thermally stable.

Glycosylated peptide-calcium chelate: Characterization, calcium absorption promotion and prebiotic effect

Finding functional preparations that could improve the bioavailability of calcium is one of the keys to solving calcium deficiency. In this study, glycosylated peptides-calcium chelate with calcium absorption promoting activity, named XOS-CSPHs-Ca-MR, was prepared from Crimson Sapper scales protein hydrolysates (CSPHs) and xylooligosaccharides (XOS) via Maillard reaction. Results showed that amino nitrogen, carboxyl oxygen, and carbonyl oxygen atom were the primary calcium chelating sites. Remarkably, XOS-CSPHs-Ca-MR exhibited good calcium phosphate crystallization inhibitory activity, gastrointestinal stability, and could promote calcium transport efficiency in the Caco-2 cell monolayer. In vitro fermentation results showed that XOS-CSPHs-Ca-MR improved the gut microbiota structure of calcium-deficient mice. Its prebiotic effect was achieved by increasing the number of beneficial bacteria, boosting the production of short-chain fatty acids, and improving the colonization ability of microbiota. Therefore, this study could lay a foundation for the study of glycosylated peptide-calcium chelate as a novel calcium supplement with prebiotic effect.

Adsorption, thermal conversion, and catalytic hydrogenation of acrolein on Cu surfaces

The adsorption, thermal chemistry, and catalytic hydrogenation of acrolein on copper model surfaces was characterized by a combination of surface-science techniques, namely, reflection–absorption infrared spectroscopy (RAIRS) and temperature program desorption (TPD), quantum mechanics (DFT) calculations, and catalytic kinetic measurements using a so-called “high-pressure cell”. Adsorption of acrolein on the Cu surface was found to involve both the carbonyl oxygen atom and the CC bond. Thermal activation leads to early dissociation and dehydrogenation to produce acetylene and carbon monoxide below 160 K, and later to the production of ketene (220 K) and propene (260 K). Under vacuum hydrogenation with H2 is not possible, but upon predosing of the surface with atomic H all the possible hydrogenation products, namely, propanal, 1-propanol, and allyl alcohol, were detected in TPD experiments, at 162, 190, and 210 K, respectively. Finally, catalytic hydrogenation under atmospheric pressures is slow and only produces propanal, at turnover frequencies below 0.2 s−1.

Perhalomethyl Chromones: Spectroscopic, X‐Ray Diffraction, Hirshfeld Surface, and Density Functional Theory Studies of the Noncovalent Interactions

AbstractThe structure of two perhalomethylated chromones, 2‐chlorodifluoromethylchromone (a) and its 6‐nitro substituted derivative (b), are investigated. The supramolecular assembly is governed by the hydrogen bond interaction (C−H···O) between the olefinic proton (OC−C(=C<)‐H) and the carbonyl oxygen atom (>C=O) giving rise to center‐symmetric graph‐set motifs. The H···O interatomic distance is shorter in (b) suggesting a stronger hydrogen bonding for this derivative. Quantum Theory of Atoms in Molecules (QTAIM) and natural bond orbital (NBO) calculated energies and the higher polarity computed for (b) agree with this experimental finding. The Molecular Electrostatic Potential (MEP) graph shows a distinctive C···Cl contact, found only for (b), involving a more electrophilic methine carbon atom.

Molybdenum-Catalyzed Intermolecular Deoxygenative Cross-Coupling Reactions of 1,2-Diketones with α-Ketoamides

Here we describe the Mo-catalyzed intermolecular deoxygenative cross coupling of the bench stable and readily accessible1,2-diketones with α-ketoamides, in which three of the four carbonyl oxygen atoms were eliminated along with the formations of a carbon–nitrogen bond and a carbon–carbon double bond in one step under Mo-catalysis. Various pyrrol-2-ones were secured in up to 96% yield by utilizing a commercial Mo-catalyst. The synthetic potential of the current methodology is additionally demonstrated by synthetic transformations, a gram-scale synthesis, and derivatization of several natural products and drug molecules. The preliminary mechanistic investigation suggest this cascade process might be initiated via the formal intermolecular N–H insertion and followed by the intramolecular carbonyl–carbonyl olefination reaction, in which both steps were catalyzed by a single Mo-catalyst.

Microhydration of Phenyl Formate: Gas-Phase Laser Spectroscopy, Microwave Spectroscopy, and Quantum Chemistry Calculations.

Herein, we have investigated the structure of phenyl formate⋅⋅⋅water (PhOF⋅⋅⋅H2 O) dimer and various non-covalent interactions present there using gas-phase laser spectroscopy and microwave spectroscopy combined with quantum chemistry calculations. Two conformers of PhOF⋅⋅⋅H2 O (C1 and T1), built on the two cis/trans conformers of the bare molecule, have been observed in the experiment. In cis-PhOF, there is an nCO → interaction between the lone-pair orbital of the carbonyl oxygen atom and the π* orbital of the phenyl ring, which persists in the monohydrated C1 conformer of PhOF⋅⋅⋅H2 O according to the NBO and NCI analyses. On the other hand, this interaction is absent in the trans-PhOF conformer as the C=O group is away from the phenyl ring. The C1 conformer is primarily stabilized by an interplay between O-H⋅⋅⋅O=C hydrogen bond and O-H⋅⋅⋅π interactions, while the stability of the T1 conformer is primarily governed by the O-H⋅⋅⋅O=C hydrogen bond. The most important finding of the present work is that the conformational preference of the PhOF monomer is retained in its monohydrated complex.

Piezo-Responsive Hydrogen-Bonded Frameworks Based on Vanillin-Barbiturate Conjugates.

A concept of piezo-responsive hydrogen-bonded π-π-stacked organic frameworks made from Knoevenagel-condensed vanillin–barbiturate conjugates was proposed. Replacement of the substituent at the ether oxygen atom of the vanillin moiety from methyl (compound 3a) to ethyl (compound 3b) changed the appearance of the products from rigid rods to porous structures according to optical microscopy and scanning electron microscopy (SEM), and led to a decrease in the degree of crystallinity of corresponding powders according to X-ray diffractometry (XRD). Quantum chemical calculations of possible dimer models of vanillin–barbiturate conjugates using density functional theory (DFT) revealed that π-π stacking between aryl rings of the vanillin moiety stabilized the dimer to a greater extent than hydrogen bonding between carbonyl oxygen atoms and amide hydrogen atoms. According to piezoresponse force microscopy (PFM), there was a notable decrease in the vertical piezo-coefficient upon transition from rigid rods of compound 3a to irregular-shaped aggregates of compound 3b (average values of d33 coefficient corresponded to 2.74 ± 0.54 pm/V and 0.57 ± 0.11 pm/V), which is comparable to that of lithium niobate (d33 coefficient was 7 pm/V).

Distinguishment of Weak Interactions of Hydrogen Atoms Bound to Carbon Atoms: X-Ray Crystal Structural and Hirshfeld Surface Analyses of 2- Hydroxy-7-methoxy-3-(2,4,6-trimethylbenzoyl)naphthalene with the 2- Methoxylated Homologue

Abstract: X-ray crystal and Hirshfeld surface analyses of 2-hydroxy-7-methoxy-3-(2,4,6- trimethylbenzoyl)naphthalene and its 2-methoxylated homologue show quantitatively and visually distinct molecular contacts in crystals and minute differences in the weak intermolecular interactions. The title compound has a helical tubular packing, where molecules are piled in a two-folded head-to-tail fashion. The homologue has a tight zigzag molecular string lined up behind each other via nonclassical intermolecular hydrogen bonds between the carbonyl oxygen atom and the hydrogen atom of the naphthalene ring. The dnorm index obtained from the Hirshfeld surface analysis quantitatively demonstrates stronger molecular contacts in the homologue, an ethereal compound, than in the title compound, an alcohol, which is consistent with the higher melting temperature of the former than the latter. Stabilization through the significantly weak intermolecular nonclassical hydrogen bonding interactions in the homologue surpasses the stability imparted by the intramolecular C=O…H–O classical hydrogen bonds in the title compound. The classical hydrogen bond places the six-membered ring in the concave of the title molecule. The hydroxy group opposingly disturbs the molecular aggregation of the title compound, as demonstrated by the distorted H…H interactions covering the molecular surface, owing to the rigid molecular conformation. The position of effective interactions predominate over the strength of the classical/nonclassical hydrogen bonds in the two compounds.