RESEARCH ON THE ANTIOXIDANT ABILITY OF 5-AMINO-1-NAPHTHOL BY HYDROGEN ATOM TRANSFER MECHANISM

Dinh Quy Huong *

* Corresponding author: (dinhquyhuong@dhsphue.edu.vn)

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Received: Apr 5, 2022
Revised: May 13, 2022
Accepted: May 20, 2022
Published: Apr 20, 2022
Title: RESEARCH ON THE ANTIOXIDANT ABILITY OF 5-AMINO-1-NAPHTHOL BY HYDROGEN ATOM TRANSFER MECHANISM
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Hương, Đ. Q. (2022). RESEARCH ON THE ANTIOXIDANT ABILITY OF 5-AMINO-1-NAPHTHOL BY HYDROGEN ATOM TRANSFER MECHANISM. Journal of Science and Education, 63(03). Retrieved from https://tckhgd.dhsphue.edu.vn/index.php/jse/article/view/340
Issue
Vol. 63 No. 03 (2022): Journal of Science: Natural Science Issue
Section
Journal of Science and Education: Natural Science - Technology

Abstract

The density functional theory has been used to study the antioxidant capacity of 5-amino-1-naphthol (NH2C10H6OH) in reaction with HOO• free radical. The hydrogen atom transfer (HAT) reaction mechanism was investigated at three positions N17–H18, N17–H19 and O20–H21 at the theoretical level wb97xd/6-311++g(d,p). The results showed that O20–H21 position was rated the most favored hydrogen transfer position with the highest rate constant of 3,6.105 M–1s–1. The reaction had the enthalpy value of -5.6 kcal.mol-1 and the Gibbs free energy of -6.4 kcal.mol-1. These proved that the reaction between HOO• and 5-amino-1-naphthol was an exothermic and spontaneous process.

Tóm tắt

Lý thuyết phiếm hàm mật độ đã được sử dụng để nghiên cứu khả năng chống oxy hóa của 5-amino-1-naphthol (NH2C10H6OH) trong phản ứng với gốc tự do HOO•. Phản ứng theo cơ chế chuyển nguyên tử hydro đã được khảo sát ở ba vị trí N17-H18, N17-H19 và O20-H21 ở mức lý thuyết wb97xd/6-311++g(d,p). Kết quả cho thấy rằng O20-H21 được đánh giá là vị trí chuyển hydro được ưu tiên nhất với tốc độ phản ứng là 3,6×105 M-1s-1. Phản ứng có giá trị hiệu ứng nhiệt là -5,6 kcal.mol-1 và năng lượng tự do Gibbs -6,4 kcal.mol-1. Điều này chứng tỏ phản ứng giữa HOO• và 5-amino-1-naphthol là quá trình tỏa nhiệt và tự diễn biến.

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References

Klein, V. Lukeš, Z. Cibulková, and J. Polovková (2006). Study of N–H, O–H, and S–H bond dissociation enthalpies and ionization potentials of substituted anilines, phenols, and thiophenols, Journal of Molecular Structure: THEOCHEM, vol.758, pp. 149-159.

Q. Huong, M. V. Bay, and P. C. Nam (2021). Antioxidant activity of thiourea derivatives: An experimental and theoretical study, Journal of Molecular Liquids, vol. 340, pp.117-149.

Matsushita, I.-C. Jang, T. Imai, K. Fukushima, J.-M. Lee, H.-R. Park, et al. (2010). Antioxidant and cytotoxic activities of naphthalene derivatives from Diospyros kaki, Journal of Wood Science, vol.57, pp.161-165.

Anand Raghunath and K. Nandibeoor Mathada, Synthesis and biological evaluation of aminonaphthols incorporated indole derivatives, Int J Med Chem, vol.2014, pp.673-206.

Sugahara, K. Fukuhara, Y. Tokunaga, S. Tsutsumi, Y. Ueda, M. Ono, et al. (2018). Radical scavenging effects of 1-naphthol, 2-naphthol, and their sulfate-conjugates, J Toxicol Sci, vol.43, pp.213-221.

Erdogan, L. Polat Kose, S. Essiz, and I. Gulcin (2021). Synthesis and biological evaluation of some 1-naphthol derivatives as antioxidants, acetylcholinesterase, and carbonic anhydrase inhibitors, Arch Pharm (Weinheim), vol. 354.

D. Chai and M. Head-Gordon (2008). Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections, Phys Chem Chem Phys, vol.10, pp.6615-20.

Galano and J. R. Alvarez-Idaboy (2013). A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity, J Comput Chem, vol.34, pp.2430-45.

Urbaniak, M. Szeląg, and M. Molski (2013). Theoretical investigation of stereochemistry and solvent influence on antioxidant activity of ferulic acid, Computational and Theoretical Chemistry, vol.1012, pp.33-40.

L. Tabrizi, D. Q. Dao, and T. A. Vu (2019). Experimental and theoretical evaluation on the antioxidan