基于密度泛函理论的肾上腺素分子的光谱分析

doi:10.3964/j.issn.1000-0593(2022)01-0248-05

Abstract
References
Related Citation (15)

Download: PDF (2557 KB)
Export: BibTeX | EndNote (RIS)

Abstract Epinephrine is a neurotransmitter and hormone transmitter. Studying the spectra and energy levels of the epinephrine molecules may help to understand their chemical stability and pharmacological effects. Based on density functional theory (DFT), the structure of epinephrine was optimized by using Software Gaussian 09 at the level of B3LYP/6-311G(d, p) in this article. On this basis, the first 20 excited states of epinephrine molecule were calculated by using the time-dependent density functional theory (TD-DFT) at the level of PBE/def2tzvp in the gas phase, and ultraviolet spectrum was drawn by using Multiwfn3.7 (dev) software and the properties of excitation are analyzed. The main transitions corresponding to the UV spectrum of adrenaline molecules are those from the ground state to the first, second, fourth, eighth, 15th and 16th excited states respectively. The oscillator strength of other excited states is lower than the threshold value of 0.03. The theoretical calculation showed two absorption peaks in the ultraviolet spectrum of epinephrine, which are located at 206.23 and 273.92 nm respectively. The peak at 206.23 nm is mainly formed from the ground state transition to the 16th excited state, and the peak at 273.92 nm is mainly formed from the ground state transition to the 2nd and 4th excited states. They are mainly produced by the transition from π band to π^* band on the benzene ring, and they are in good agreement with the experimental spectrum. The analysis of the excited state properties of adrenergic molecules shows that the absorption peaks are generated in the adjacent orbital transitions of the highest occupied orbital and the lowest vacant orbital. Then, the PBE method based on density functional theory was used to calculate the infrared frequency and draw the infrared spectrum of adrenergic molecules at the base group level of 6-311g (d, p). The vibration analysis shows that the characteristic absorption peak is generated by the phenol hydroxyl O—H vibration at 3 738 and 3 662 cm^-1, and the alcohol hydroxyl O—H vibration generates the characteristic absorption peak at 3 715 cm^-1. Point 2 854 cm^-1 is the characteristic absorption peak generated by the stretching vibration of the C18—H20 bond of methyl, point 1 516 and 1 439 cm^-1 are the characteristic absorption peaks of the stretching vibration of the benzene ring, at 1 279 and 1 057 cm^-1 respectively were the characteristic absorption peak of the stretching vibration of the C6—O10 and C12—O23 bond, and point 620 cm^-1 is the characteristic absorption peak of the oscillation of the N22—H17 bond. The vibration analysis is consistent with the characteristic absorption peaks of various functional groups in the introduction to spectroscopy. By comparing the experimental infrared spectrum of epinephrine, it was found that the characteristic absorption peaks of each group in the theoretical spectrum were relatively obvious, and they were generally in good agreement with the experimental spectrum. Due to the hydrogen bond formed between the adrenergic molecular dimer and the polymer, the hydrogen bond formed between the molecules weakens the strength of the O—H bond. It reduces the stretching vibration frequency of the hydroxyl O—H that can form the inter-molecular hydrogen bond, which results in a wide peak of the experimental spectrum between 3 500 and 2 500 cm^-1.

Key words：Epinephrine; Density functional theory; UV spectrum; Infrared spectrum (IR)

Received: 2020-12-10 Accepted: 2021-03-19

ZTFLH:

R971+.93

Corresponding Authors: TANG Yan-lin E-mail: tylgzu@163.com

Cite this article:

URL:

https://www.gpxygpfx.com/EN/10.3964/j.issn.1000-0593(2022)01-0248-05 OR https://www.gpxygpfx.com/EN/Y2022/V42/I01/248

[1] LIU Miao, BI Jin, GUO Xia-zhen, et al(刘淼, 毕晋, 郭霞珍, 等). World Chinese Medicine(世界中医药), 2020, 15(6): 925.
[2] GUAN Kai-xing, WANG Wen-jing, LI Zi-jian(关开行, 王文景, 李子健). Science China Life Sciences(中国科学: 生命科学), 2020, 50(8): 791.
[3] LI Ping, ZHANG Fu-tian, LIU Gang, et al(李萍, 张福田, 刘刚, 等). Journal of University of Science and Technology of China(中国科学技术大学学报)，2013, 43(2): 135.
[4] ZHANG Zhan-jun, LI Jing-jian, WU Xi-zun(张占军, 李经建, 吴锡尊). Acta Phys.-Chim. Sin.(物理化学学报), 2001, 17(6): 542.
[5] WEI Guo, LIANG Jie, LI Yu-peng, et al(魏国, 梁杰, 李玉鹏, 等). Chinese General Practice(中国全科医学), 2016, 19(3): 327.
[6] Wang Xiaoqin, Li Shiyi, Zhao Liang, et al. Chinese Journal of Chemical Engineering, 2020, 28(2): 532.
[7] ZHAO San-hu, JIA Xiao-li(赵三虎, 贾晓丽). Chemistry(化学通报), 2015, 78(3): 285.
[8] YU Jian-cheng, TANG Yan-lin, CHANG Rui, et al(于建成, 唐延林, 常瑞, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2019, 39(6): 1846.
[9] ZHONG Yu-jie, LU Li-min, LI Jia-hui, et al(钟玉洁, 陆利敏, 李佳会, 等). Journal of Atomic and Molecular Physics(原子与分子物理学报), 2020, 37(2): 157.
[10] LI Lin, YANG Bao-hua, ZHANG Ai-hua(李琳, 杨宝华, 张爱华). Chinese Journal of Chemical Education·Chinese and English(化学教育·中英文), 2020, 41(24): 92.
[11] Lu Tian, Chen Feiwu. Multiwfn: A Multifunctional Wavefunction Analyzer，2012, 33(5): 580.
[12] Seema Shukla, Anubha Srivastava, Padam Kumar, et al. Vibrational spectroscopic, 2020, 1244: 128443.
[13] Shanghai Institute of Organic Chemistry of CAS. Chemistry Database[DB/OL]. http://www.organchem.csdb.cn. [1978-2020]
[14] ZHU Ming-chen, BAO Ying, YE Yu-yuan(朱明臣, 鲍颖, 叶余原). Contemporary Chemical Industry(当代化工), 2015, 44(5): 904.
[15] LU Tian. Molclus program, Version 1.9.6, http://www.keinsci.com/research/molclus.html. [2020-11-20]