|
|
|
|
|
|
| Terahertz Spectroscopic Investigation of Maleic Hydrazide Polymorphs |
| ZHENG Zhuan-ping, LI Ai-dong, DONG Jun, ZHI Yan, GONG Jia-min |
School of Electronic Engineering, Xi’an University of Posts and Telecommunications, Xi’an 710121, China
|
|
|
|
|
Abstract Polymorphs refer to substances with the same chemical composition but in more than one crystal form. These polymorphs exist widely in nature, especially in pharmaceuticals. These polymorphs have the same chemical molecular composition, but their physical and chemical properties are different, ultimately affecting the effect of pharmaceuticals. In recent years, with the generation of terahertz (THz) wave becoming a conventional technology, the application fields of terahertz time-domain spectroscopy (THz-TDS) has been gradually broadened. THz wave is related to intramolecular interaction mode and closely related to weak interaction modes such as hydrogen bond and van der Waals force. THz radiation can induce low-frequency bond vibration, crystal phonon vibration, hydrogen bond stretching and torsional vibration, and the collective vibration modes of many organic molecules are located in this region, especially pharmaceutical molecules. Thus in this paper, THz-TDS was used to study the THz absorption spectra of maleic hydrazide polymorphs (MH2 and MH3) in the range of 0.25~2.25 THz. The experimental results show that the THz absorption peaks of MH2 and MH3 are completely different. Specifically, MH2 has three characteristic absorption peaks, which are located at 0.34, 1.41 and 1.76 THz. MH3 has two characteristic absorption peaks at 0.75 and 1.86 THz. These results show that the polymorphs of maleic hydrazide can be distinguished and characterized by their THz absorption peaks. Then, to analyze the THz experimental peaks, solid-state density functional theory (DFT) is used to simulate. In matching experimental and theoretical spectral data, the origins of the THz absorption peaks are analyzed and discussed. The results suggest that the THz absorption peaks of MH2 and MH3 are very sensitive to their three-dimensional structures, and the absorption peaks all originate from intermolecular interactions Finally, the THz spectra of the commercial tablets of maleic hydrazide were tested. By comparing the THz absorption peaks between MH2(MH3) and Qingxiansu, it is found that the crystal form of Qingxiansu is MH3. This result shows that THz-TDS is a potential tool for detecting pharmaceutical polymorphism. Our research is expected to promote the detection of maleic hydrazide polymorphs in industrial production and clinical application.
|
|
Received: 2021-04-06
Accepted: 2021-05-26
|
|
|
|
[1] Gandhi R B, Bogardus J B, Bugay D E, et al. International Journal of Pharmaceutics, 2000, 201(2): 221.
[2] Khankari R, Chen L, Grant D. Journal of Pharmaceutical Sciences, 1998, 87: 1052.
[3] Suryanara Yanan, Herman C. Pharm. Res., 1991, 8: 393.
[4] Phadnis N, Cavatur R, Husdon B, et al. J. Pharm. Biomed. Anal., 1997, 15: 929.
[5] Patel A D, Luner P E, Kemper M S. Int. J. Pharm., 2000, 206(1): 63.
[6] Takasuka M, Nakai H. Vib. Spec., 2001, 25: 197.
[7] DU Yong, XIA Yan, TANG Wen-jian, et al(杜 勇, 夏 燚, 汤文建, 等). Infrared and Laser Engineering(红外与激光工程), 2014, 43(9): 2919.
[8] Delaney S P, Witko E M, Smith T M, et al. Journal of Physical Chemistry A, 2012, 116(30): 8051.
[9] CHEN Tao, CAI Zhi-hua, HU Fang-rong，et al(陈 涛, 蔡治华, 胡放荣, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析) 2019, 39(3): 686.
[10] Oppenheim K C, Korter T M, Melinger J S, et al. Journal of Physical Chemistry A, 2010, 114(47): 12513.
[11] Taday P F, Bradley I V, Arnone D D, et al. Journal of Pharmaceutical Sciences, 2003, 92(4): 831.
[12] Cradwick P D. Journal of the Chemical Society Perkin Transactions, 1976, 2(12): 1386.
[13] Katrusiak A. Acta Cryst.，1993，CA9: 36.
[14] Katrusiak A. Acta Cryst.，2001，B57: 697.
[15] Morzyk-Ociepa B. Vibrational Spectroscopy, 2008, 46(2): 115.
[16] Qu F, Pan Y, Lin L, et al. Journal of Infrared, Millimeter, and Terahertz Waves, 2018, 39: 1015.
[17] Segall M D, Lindan P, Probert M J, et al. Journal of Physics—Condensed Matter, 2002, 14(11): 2717.
[18] Perdew J P, Burke K, Ernzerhof M. Phys. Rev. Lett.，1996, 77: 3865.
[19] Troullier N, Martins J L. Phys. Rev., 1991, B43: 1993.
[20] Zhang B, Li S, Wang C, et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 190: 40.
|
| [1] |
BAI Xi-lin1, 2, PENG Yue1, 2, ZHANG Xue-dong1, 2, GE Jing1, 2*. Ultrafast Dynamics of CdSe/ZnS Quantum Dots and Quantum
Dot-Acceptor Molecular Complexes[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 56-61. |
| [2] |
WAN Mei, ZHANG Jia-le, FANG Ji-yuan, LIU Jian-jun, HONG Zhi, DU Yong*. Terahertz Spectroscopy and DFT Calculations of Isonicotinamide-Glutaric Acid-Pyrazinamide Ternary Cocrystal[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3781-3787. |
| [3] |
ZHANG Yan-dong1, WU Xiao-jing1*, LI Zi-xuan1, CHENG Long-jiu2. Two-Dimensional Infrared Spectroscopic Study of Choline
Chloride/Glycerin Solution Disturbed by Temperature[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3047-3051. |
| [4] |
YU De-guan1, CHEN Xu-lei1, WENG Yue-yue2, LIAO Ying-yi3, WANG Chao-jie4*. Computational Analysis of Structural Characteristics and Spectral
Properties of the Non-Prodrug-Type Third-Generation
Cephalosporins[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3211-3222. |
| [5] |
LI Yang1, LI Xiao-qi1, YANG Jia-ying1, SUN Li-juan2, CHEN Yuan-yuan1, YU Le1, WU Jing-zhu1*. Visualisation of Starch Distribution in Corn Seeds Based on Terahertz Time-Domain Spectral Reflection Imaging Technology[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(09): 2722-2728. |
| [6] |
WANG Yi-ru1, GAO Yang2, 3, WU Yong-gang4*, WANG Bo5*. Study of the Electronic Structure, Spectrum, and Excitation Properties of Sudan Red Ⅲ Molecule Based on the Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(08): 2426-2436. |
| [7] |
LIU Guo-peng1, YOU Jing-lin1*, WANG Jian1, GONG Xiao-ye1, ZHAO Yu-fan1, ZHANG Qing-li2, WAN Song-ming2. Application of Aerodynamic Levitator Laser Heating Technique: Microstructures of MgTi2O5 Crystal and Melt by in-situ Superhigh Temperature Raman Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(08): 2507-2513. |
| [8] |
TANG Yan1, YANG Yun-fan1, HU Jian-bo1, 2, ZHANG Hang2, LIU Yong-gang3*, LIU Qiang-qiang4. Study on the Kinetic Process and Spectral Properties of the Binding of Warfarin to Human Serum Protein[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(07): 2099-2104. |
| [9] |
SUN Zhi-shen1, LIU Yong-gang2, 3, ZHANG Xu1, GUO Teng-xiao1*, CAO Shu-ya1*. Study on the Near-Infrared Spectra of Sarin Based on Density
Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(06): 1765-1769. |
| [10] |
ZHENG Zhi-jie1, LIN Zhen-heng1, 2*, XIE Hai-he2, NIE Yong-zhong3. The Method of Terahertz Spectral Classification and Identification for Engineering Plastics Based on Convolutional Neural Network[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1387-1393. |
| [11] |
LIANG Xiao-rui1, CONG Jing-xian2, LI Yin1, LIU Jie1, JIN Liang-jie1, SUN Xiao-wei1, LI Xiao-dong3. Study on Vibrational Spectra of Cypermethrin Based on Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1381-1386. |
| [12] |
CI Cheng-gang*, ZANG Jie-chao, LI Ming-fei*. DFT Study on Spectra of Mn-Carbonyl Molecular Complexes[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1434-1441. |
| [13] |
WANG Yu-ye1, 2, LI Hai-bin1, 2, JIANG Bo-zhou1, 2, GE Mei-lan1, 2, CHEN Tu-nan3, FENG Hua3, WU Bin4ZHU Jun-feng4, XU De-gang1, 2, YAO Jian-quan1, 2. Terahertz Spectroscopic Early Diagnosis of Cerebral Ischemia in Rats[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(03): 788-794. |
| [14] |
AN Huan1, YAN Hao-kui2, XIANG Mei1*, Bumaliya Abulimiti1*, ZHENG Jing-yan1. Spectral and Dissociation Characteristics of p-Dibromobenzene Based on External Electric Field[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(02): 405-411. |
| [15] |
XU Meng-lei1, 2, GAO Yu3, ZHU Lin1, HAN Xiao-xia1, ZHAO Bing1*. Improved Sensitivity of Localized Surface Plasmon Resonance Using Silver Nanoparticles for Indirect Glyphosate Detection Based on Ninhydrin Reaction[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(01): 320-323. |
|
|
|
|
