|
|
|
|
|
|
| Terahertz Spectroscopy of the Structural Isomers of Pyridine Dicarboxylic Acid |
| LUO Guo-fang1, QI Ji2, LIU Ya-li2, HE Ming-xia2, HUANG Hua3, QU Qiu-hong2*, ZHANG Yi-zhu2* |
1. State Grid Shanghai Electric Power Research Institute, Shanghai 200437, China
2. School of Precision Instrument and Optoelectronic Engineering, Tianjin University, Tianjin 300072，China
3. State Grid Shanghai Electric Power Company, Shanghai 200437, China
|
|
|
|
|
Abstract In the production processes of food and pharmaceuticals, the identification and differentiation of stereoisomers constitute a crucial and complex issue, particularly when their molecular formulas are identical, but their crystal structures differ. Pyridine dicarboxylic acids serve as key intermediates widely used in pharmaceutical synthesis, where effective discrimination between different isomers is essential due to their varied physical and chemical properties. The technique of terahertz spectroscopy has emerged as a novel approach for detecting stereoisomers, employing high-resolution terahertz time-domain spectrometers to measure 2,3-pyridine dicarboxylic acid, 2,4-pyridine dicarboxylic acid, 2,5-pyridine dicarboxylic acid, 3,4-pyridine dicarboxylic acid, and 3,5-pyridine dicarboxylic acid, revealing their unique terahertz absorption features at different mass fractions. These isomers exhibit distinct absorption characteristics in the terahertz range. Through density functional theory calculations, a comparison between theoretical simulations and experimental measurements has been conducted, elucidating the primary vibrational modes of these compounds, encompassing the torsional vibrations of carboxyl groups and pyridine rings, bond angle bending, and their coupling effects. The research has demonstrated the unique advantages of terahertz spectroscopy in material identification, highlighting its significant differences from infrared spectroscopy. The findings not only offer insights into the terahertz spectral features of pyridine dicarboxylic acid derivatives but also showcase the potential applications of terahertz spectroscopy in the analysis and identification of chemical substances, providing new foundations for the synthesis and discrimination of pharmaceutical intermediates.
|
|
Received: 2024-01-22
Accepted: 2024-07-01
|
|
|
|
Corresponding Authors:
QU Qiu-hong, ZHANG Yi-zhu
E-mail: zhangyizhu@tju.edu.cn; quqiuhong114@126.com
|
|
[1] Frisch M, Cahill C. Dalton Transactions, 2006, 39：4679.
[2] Bawuah P, Zeitler J A. TRAC Trends in Analytical Chemistry, 2021, 139: 116272.
[3] Liu Q C, Deng H, Li H Z, et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, 283: 121722.
[4] Du S, Su M, Wang C, et al. Analytical Chemistry, 2022, 94(6): 2891.
[5] Hafez H A, Chai X, Ibrahim A, et al. Journal of Optics, 2016, 18(9): 093004.
[6] Castro-Camus E, Johnston M B. Chemical Physics Letters, 2008, 455：289.
[7] Vereecken L, Pierloot K, Peeters J. The Journal of Chemical Physics, 1998, 108(3): 1068.
[8] Orio M, Pantazis D A, Neese F. Photosynthesis Research, 2009, 102(2-3): 443.
[9] Jursic B S. Journal of Molecular Structure: THEOCHEM, 2000, 507(1-3): 185.
[10] Popov A A, Kareev I E, Shustova N B, et al. Journal of the American Chemical Society, 2007, 129(37): 11551.
[11] Yu B L, Alimova A, Katz A, et al. THz Absorption Spectrum of Bacillus Spores. Proceedings of SPIE, Terahertz and Gigahertz Electronics and Photonics IV, 2005, 5727: 20.
[12] Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 16, Revision A.03, Gaussian, Inc., Wallingford CT, 2016.
[13] Zhao Y, Truhlar D G. Theoretical Chemistry Account，2008, 120: 215
[14] Krishnan R, Binkley J S, et. al. The Journal of Chemical Physics, 1980, 72(1): 650.
[15] Grimme S, Antony J, Ehrlich S, et al. The Journal of Chemical Physics, 2010, 132: 154104.
[16] Grimme S, Ehrlich S，Goerigk L. Journal of Computational Chemistry，2011, 32：1456.
[17] Michal H Jamróz. Vibrational Energy Distribution Analysis VEDA 4, Warsaw, 2004-2010.
|
| [1] |
ZHU Yi-feng1, 3, LIU Jin-peng1, 3, SONG Zheng-xun1, 3*, ZHOU Xiao-jun4*, ZHOU Mei5, REN Jiao-jiao2, 3, YANG Wen-tao2, CUI Zong-yu2, 3. Study of Differential Diagnosis of Early NPC and Nasopharyngitis Based on THz Spectra[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(04): 941-946. |
| [2] |
LI Yi-nuo1, LIANG Xiao-rui1*, ZHANG Ji-lei1, LI Yin1, LI Xiao-dong2. Theoretical Calculation and Experimental Study on the Vibration Spectra of Ergosterol Peroxide[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(03): 623-630. |
| [3] |
WANG Shu-dong1, 3*, WANG Ye1, 3, HOU Xian-fa4, GAO Ming-shun4, ZHANG Yan2*. DFT and Experimental Study on Raman Spectroscopy of Ketamine[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(03): 672-677. |
| [4] |
GAO Wen-han1, CAI Yu-yao1, HAN Bo-yuan1, FENG Jun1, LIU Yu-zhu1, 2*. Investigation of Spectral Characteristics of Xylene Molecules Based on
Laser Raman Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(02): 332-336. |
| [5] |
ZHANG Tong-jun, HAO Jian-jun. Terahertz Absorption Spectra Simulation of Anthraquinone Based on
Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(02): 337-343. |
| [6] |
XU Jia-zhen1, WANG Chang-jiang1, WANG Chao-jie2*. Theoretical Study on the Structure and Properties of a Novel Diterpenoid Lactone Compound Euphorikanin A[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(02): 371-378. |
| [7] |
GE Jing1, 2, LI Zhi-biao1, 2, XUE Bing-qian1, 2, BAI Xi-lin1, 2*. Impact of Fluorine Substitution on the Ultrafast Dynamic Processes of
Coumarin Molecules[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(11): 3128-3135. |
| [8] |
GUO Ya-jing1, LI Xiu-yan2. Density-Functional Theory Study of the Structural and Spectrum
Properties for C15NO4HnIm (n=11, 12, 13, m=4, 3, 2, n+m=15)[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(11): 3142-3148. |
| [9] |
TANG Yan1, 3, WU Jia1, XU Jian-jie2*, GUO Teng-xiao2, HU Jian-bo1, 4, ZHANG Hang4, LIU Yong-gang5*, YANG Yun-fan4. Analysis of Near-Infrared Anharmonic Vibration Spectra of Amino Acids
Using Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(11): 3149-3156. |
| [10] |
HUANG Yu-lei1, 2, LI Wei-xing1, 2, ZHU Mei-qiang1, 2*, ZHANG Nan3, 4, KE Lin5, ZOU Liang1, 2. Thin Coatings Thickness Detection of CFRP Based on Terahertz
Time-Domain Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(10): 2753-2760. |
| [11] |
ZHANG Hong-tao, WANG Long-jie*, TAN Lian, ZHAO Xin-tao, TIAN Cheng-hao. Research Progress of Terahertz Spectroscopy Technology in Food
Contamination Detection[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(08): 2120-2126. |
| [12] |
HUANG Ji-chong1, SONG Shao-zhong2*, LIU Chun-yu1, XU Li-Jun1, CHEN An-liang1, LU Ming1, GUO Wen-jing1, MIAO Zhuang1, LI Chang-ming1, TAN Yong1, LIU Zhe3. Research on Identification of Corn Storage Years Based on Raman
Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(08): 2166-2173. |
| [13] |
YUAN Yuan1, ZHANG Tian-yao1*, ZHANG Zhao-hui1, ZHAO Xiao-yan1, LI Xing-yue1, LI Bo-yang1, WU Xian-hao1, XU Bo1, YAN Jian-feng2, SUN Pu2, CAO Can3. Non-Contact Characterization Method of Birefringence Crystal Based on Terahertz Time-Domain Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(08): 2334-2339. |
| [14] |
LI Chang-ming1, GU Yi-fan2, ZHANG Hong-chen1, SONG Shao-zhong3*, GAO Xun2*. The Surface Enhanced Raman Spectroscopy Characteristics of Cyromazine Molecule Based on Density Function Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(06): 1566-1570. |
| [15] |
WANG Yang1, LIN Zhen-heng2, 1*, ZHENG Zhi-jie1, XIE Hai-he2, NIE Yong-zhong3. Lifetime Prediction Method for Fluororubber Based on Terahertz Time Domain Spectrum Technology[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(06): 1578-1583. |
|
|
|
|
