Molecular structure and internal dynamics of the antioxidant 2,6-di-tert-butylphenol

Li, Wenqin; Maris, Assimo; Melandri, Sonia; Lesarri, Alberto; Evangelisti, Luca

doi:10.1016/j.molstruc.2023.136910

Cited by 4 publications

(4 citation statements)

References 36 publications

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“…This type of motion is similar to that observed in the monomer and molecules with the same structural framework, such as phenol [7][8][9][10] or p-cresol [12]. In the case of 26BP [6], however, each individual transition is further split into three components whose characteristics are described later in this paper. These splittings led to the assignment of three pairs of torsional states, denoted 0-1, 2-3, and 4-5 as can be seen in Figure 2.…”

Section: Resultssupporting

confidence: 71%

The Structure of 2,6-Di-tert-butylphenol–Argon by Rotational Spectroscopy

Li,

Maris,

Melandri

et al. 2023

Molecules

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The molecular structure of a van der Waals-bonded complex involving 2,6-di-tert-butylphenol and a single argon atom has been determined through rotational spectroscopy. The experimentally derived structural parameters were compared to the outcomes of quantum chemical calculations that can accurately account for dispersive interactions in the cluster. The findings revealed a π-bound configuration for the complex, with the argon atom engaging the aromatic ring. The microwave spectrum reveals both fine and hyperfine tunneling components. The main spectral doubling is evident as two distinct clusters of lines, with an approximate separation of 179 MHz, attributed to the torsional motion associated with the hydroxyl group. Additionally, each component of this doublet further splits into three components, each with separations measuring less than 1 MHz. Investigation into intramolecular dynamics using a one-dimensional flexible model suggests that the main tunneling phenomenon originates from equivalent positions of the hydroxyl group. A double-minimum potential function with a barrier of 1000 (100) cm−1 effectively describes this extensive amplitude motion. However, the three-fold fine structure, potentially linked to internal motions within the tert-butyl group, requires additional scrutiny for a comprehensive understanding.

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Section: Resultssupporting

confidence: 71%

The Structure of 2,6-Di-tert-butylphenol–Argon by Rotational Spectroscopy

Li,

Maris,

Melandri

et al. 2023

Molecules

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“…Unfortunately, the highly complex and dense spectrum did not allow for a satisfactory interpretation. The same kind of splitting was then observed in the 26BP⋅⋅⋅argon complex [12] . The analysis of the rotational spectrum of the monomer complexed with argon revealed that breaking the symmetry on a plane perpendicular to the ring did not modify the observed splittings, confirming the nature of the hydroxyl group motion toward the two tert ‐butyl groups.…”

Section: Introductionsupporting

confidence: 64%

“…Recently, we reported the analysis of the rotational spectrum of the important antioxidant 2,6-di-tert-butylphenol (26BP). [6] This molecule features the structure of phenol with a hydroxyl group attached to a benzene ring [7] and two tert-butyl groups at symmetric ortho positions relative to the hydroxyl group. While the molecular structure was detailed, the analysis of the rotational spectrum presented challenges that have not been fully resolved.…”

Section: Introductionmentioning

confidence: 99%

A Rotational Study of 2‐tert‐Butylphenol and Its 1 : 1 Argon Complex

Li,

Heras,

Maris

et al. 2024

ChemPhysChem

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The chirped‐pulse Fourier Transform microwave spectrum of 2‐tert‐butylphenol, an industrial intermediate for the production of antioxidants, has been investigated in the 2‐8 GHz frequency range. The spectral analysis has allowed obtaining precise structural information on the most stable conformer and its complex with argon. The conformation of the monomer reveals that the hydroxyl group is coplanar with the ring but points in the opposite direction to the tert‐butyl group, reducing steric interactions. In the terbutyl group one methyl group is coplanar and the other two are symmetrically staggered respect to the ring. The complex shows the rare gas sitting above the aromatic ring. Interestingly, neither the monomer nor the complex do not exhibit large‐amplitude hydroxyl torsion motions, previously observed in 1,6‐disubstituted phenols such as 2,6‐di‐tert‐butylphenol or propofol. The experimental results are supported by computational calculations, validating the molecular structure. Additionally, symmetry‐adapted perturbation theory has allowed for determining the van der Waals intermolecular interaction energy of the complex.

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“…Cosmetics analysis represents a rapidly expanding field of analytical chemistry, as new cosmetic formulations are increasingly in demand on the market and the ingredients required for their production are constantly evolving. In particular, the addition of antioxidants, which are well established in food, beverages, and pharmaceuticals, is becoming increasingly popular in cosmetic preparations, where they can serve as active ingredients, supplements, and stabilizers [1][2][3][4][5][6]. Indeed, their ability to scavenge free radicals provides anti-aging, photoprotective, antimicrobial, and anti-inflammatory action, along with protection against oxidative degradation of product components, such as lipid rancidity [1].…”

Section: Introductionmentioning

confidence: 99%

Easy-to-Use Chemiluminescent-Based Assay for a Rapid and Low-Cost Evaluation of the Antioxidant Activity of Cosmetic Products

Pour,

Calabria,

Nascetti

et al. 2024

Chemosensors

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New cosmetic formulations are continuously requested by the market and the ingredients are constantly evolving. Recently the use of antioxidants has gained success and, in this context, analytical methods able to quickly and easily assess the antioxidant activity of cosmetics would make it possible to carry out analyses on new formulations even within the manufacturing process without the need for specialized laboratories and personnel, thus evaluating directly on-site the effectiveness and the shelf life of products. In this work, a chemiluminescent inhibition assay was developed for determining the total antioxidant activity in cosmetic products. The method was based on the luminol/enhancers/hydrogen peroxide/horseradish peroxidase chemiluminescent system, which generates light signals measurable through simple and compact instrumentation. The formation of the chemiluminescent signal is inhibited by the presence of antioxidant substances while it is restored once all the antioxidant molecules have been oxidized. The time of appearance of the light signal is related to the total antioxidant activity. The assay was carried out exploiting an integrated device comprising a microwell plate coupled with an array of amorphous silicon hydrogenated photosensors enclosed in a mini-dark box. The method was optimized in terms of concentrations and volumes of the required reagents and sample pre-treatment. A calibration curve was generated taking as a reference the antioxidant activity of ascorbic acid obtaining a detection limit of 10 µM. The developed method was applied to cosmetic products currently on the market as well as on spiked samples in order to evaluate the performance of the methods in terms of sensitivity, accuracy, and reproducibility.

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Molecular structure and internal dynamics of the antioxidant 2,6-di-tert-butylphenol

Cited by 4 publications

References 36 publications

The Structure of 2,6-Di-tert-butylphenol–Argon by Rotational Spectroscopy

The Structure of 2,6-Di-tert-butylphenol–Argon by Rotational Spectroscopy

A Rotational Study of 2‐tert‐Butylphenol and Its 1 : 1 Argon Complex

Easy-to-Use Chemiluminescent-Based Assay for a Rapid and Low-Cost Evaluation of the Antioxidant Activity of Cosmetic Products

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