| Peer-Reviewed

Analysis of the Alcohol Amine Mixtures by 1D Selective COSY

Received: 18 March 2022     Published: 23 March 2022
Views:       Downloads:
Abstract

Proton nuclear magnetic resonance (1H-NMR) is one of the most commonly used techniques for structure identification in the field of chemical warfare convention (CWC) because of its strong ability in aiding structure assignment of chemicals. However, due to the lack of separation function coupled with chromatograph, the greatest disadvantage of 1H-NMR in the analysis of environmental and biological samples is that the resonances can be easily covered or interfered. One-dimensional NMR selective excitation technology can effectively remove background interference and reveal the hidden spectral peak information. In this paper, three schedule chemicals of Chemical Weapons Convention (CWC), triethanolamine, N-methyldiethanolamine and 2-diisopropylaminoethanol, were selected as model chemicals. Homonuclear 1D COSY NMR selective excitation analysis method was established with these chemicals to solve the problem of resonances covered in 1H-NMR. Key experiment parameters of 1D COSY were optimized. The optimized experimental conditions of 1D COSY are as follows: pulse sequence is selcogp, shaped pulse is G3, relaxation delay of d1 is 4 s, the excitation width of dH 0.91 (a), 2.51 (g), 2.62 (e) and 3.44 (d) is 39.16, 35.34, 20.00 and 26.03 Hz respectively. The established 1D COSY method was used to analyze 1~10 μg/mL alcohol amine mixtures with 2 mg/mL quinuclidinol as the background interference and the LOD was 5 μg/mL. This method is simple, fast and can wipe off the interference effectively in the 1H NMR spectrum without proceeding complex sample pretreatment. 1D selective COSY reflects the more accurate position of hydrogen atom, and can be used as a reliable auxiliary technology for structural identification.

Published in Modern Chemistry (Volume 10, Issue 1)
DOI 10.11648/j.mc.20221001.12
Page(s) 5-11
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2022. Published by Science Publishing Group

Keywords

Precursors of Chemical Weapon, Selective Excitation, 1D COSY, Mixture, Alcohol Amine

References
[1] Claridge T D W. High-resolution NMR techniques in organic chemistry [M]. Elsevier Books, 2001: 12-13.
[2] Htun K T, Pan J, Pasanta D, et al. Identification of Metabolic Phenotypes in Young Adults with Obesity by 1H NMR Metabolomics of Blood Serum [J]. Life, 2021, 11 (6): 574.
[3] Sulaiman F, Azam A A, Bustamam M, et al. Metabolite Profiles of Red and Yellow Watermelon (Citrullus lanatus) Cultivars Using a 1H-NMR Metabolomics Approach [J]. Molecules, 2020, 25 (14).
[4] Shumilina E, Andreasen C, Bitarafan Z, et al. Determination of Glyphosate in Dried Wheat by 1H-NMR Spectroscopy [J]. Molecules, 2020, 25 (7).
[5] Guo C, Fritz M P, Struppe J, et al. Fast 19 F Magic Angle Spinning NMR Crystallography for Structural Characterization of Fluorine-Containing Pharmaceutical Compounds [J]. Analytical Chemistry, 2021.
[6] Zhang L, Gellerstedt G. Quantitative 2D HSQC NMR determination of polymer structures by selecting suitable internal standard references [J]. Magnetic Resonance in Chemistry Mrc, 2011, 45 (1): 37-45.
[7] Changlun, Shao, Zhigang, et al. 1H and 13C NMR assignments for two anthraquinones and two xanthones from the mangrove fungus (ZSUH-36) [J]. Magnetic Resonance in Chemistry, 2007.
[8] Brennan, Lorraine. NMR-based metabolomics: from sample preparation to applications in nutrition research. [J]. Prog Nucl Magn Reson Spectrosc, 2014, 83: 42-49.
[9] Halabalaki, Bertrand, Stefanou, et al. Sample Preparation Issues in NMR-based Plant Metabolomics: Optimisation for Vitis Wood Samples [J]. PHYTOCHEM ANALYSIS, 2014.
[10] Kim H, Jung C, Lee Y. Analysis Study on 32nd OPCW Proficiency Test Sample with GC-TSQ CI [J]. Journal of the Korea Institute of Military Science and Technology, 2014, 17 (6): 828-835.
[11] Uhrinova S, Du X, An U, et al. Detection of long-range couplings in oligomers and evaluation of coupling constants in polymers. Application of the 1D COSY technique [J]. Magnetic Resonance in Chemistry, 1991, 29 (1): 144-147.
[12] Pham T N, Liptaj T, Barlow P N, et al. J-modulated 1D directly COSY for precise measurement of proton-proton residual dipolar coupling constants of oligosaccharides [J]. Magnetic Resonance in Chemistry, 2011, 40 (11).
[13] Stryjewski D, Oschkinat H, Leibfritz D. Detection of metabolites in body fluids and biological tissue by a 1D soft COSY technique [J]. Magnetic Resonance in medicine Official Journal of the Society of Magnetic Resonance in Medicine, 1990, 13 (1): 158.
[14] Dioukhane K, Aouine Y, Nakkabi A, et al. Characterization of the Structure of 2-(4-methyl-2 Phenyl-4, 5-dihydrooxazol-4-ylmethyl)-isoindole-1, 3-dione by 1D, COSY and HSQC 2D NMR Spectroscopy [J]. Asian Journal of Chemical Sciences, 2021: 30-37.
[15] Hu H, Bradley S A, Krishnamurthy K. Extending the limits of the selective 1D NOESY experiment with an improved selective TOCSY edited preparation function [J]. Journal of Magnetic Resonance, 2004, 171 (2): 201-206.
[16] Howe P. Removal of zero-quantum peaks from 1D selective TOCSY and NOESY spectra [J]. Journal of Magnetic Resonance, 2006, 179 (2): 217-222.
Cite This Article
  • APA Style

    Zhang He, Huang Guilan, Yang Hongyu. (2022). Analysis of the Alcohol Amine Mixtures by 1D Selective COSY. Modern Chemistry, 10(1), 5-11. https://doi.org/10.11648/j.mc.20221001.12

    Copy | Download

    ACS Style

    Zhang He; Huang Guilan; Yang Hongyu. Analysis of the Alcohol Amine Mixtures by 1D Selective COSY. Mod. Chem. 2022, 10(1), 5-11. doi: 10.11648/j.mc.20221001.12

    Copy | Download

    AMA Style

    Zhang He, Huang Guilan, Yang Hongyu. Analysis of the Alcohol Amine Mixtures by 1D Selective COSY. Mod Chem. 2022;10(1):5-11. doi: 10.11648/j.mc.20221001.12

    Copy | Download

  • @article{10.11648/j.mc.20221001.12,
      author = {Zhang He and Huang Guilan and Yang Hongyu},
      title = {Analysis of the Alcohol Amine Mixtures by 1D Selective COSY},
      journal = {Modern Chemistry},
      volume = {10},
      number = {1},
      pages = {5-11},
      doi = {10.11648/j.mc.20221001.12},
      url = {https://doi.org/10.11648/j.mc.20221001.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221001.12},
      abstract = {Proton nuclear magnetic resonance (1H-NMR) is one of the most commonly used techniques for structure identification in the field of chemical warfare convention (CWC) because of its strong ability in aiding structure assignment of chemicals. However, due to the lack of separation function coupled with chromatograph, the greatest disadvantage of 1H-NMR in the analysis of environmental and biological samples is that the resonances can be easily covered or interfered. One-dimensional NMR selective excitation technology can effectively remove background interference and reveal the hidden spectral peak information. In this paper, three schedule chemicals of Chemical Weapons Convention (CWC), triethanolamine, N-methyldiethanolamine and 2-diisopropylaminoethanol, were selected as model chemicals. Homonuclear 1D COSY NMR selective excitation analysis method was established with these chemicals to solve the problem of resonances covered in 1H-NMR. Key experiment parameters of 1D COSY were optimized. The optimized experimental conditions of 1D COSY are as follows: pulse sequence is selcogp, shaped pulse is G3, relaxation delay of d1 is 4 s, the excitation width of dH 0.91 (a), 2.51 (g), 2.62 (e) and 3.44 (d) is 39.16, 35.34, 20.00 and 26.03 Hz respectively. The established 1D COSY method was used to analyze 1~10 μg/mL alcohol amine mixtures with 2 mg/mL quinuclidinol as the background interference and the LOD was 5 μg/mL. This method is simple, fast and can wipe off the interference effectively in the 1H NMR spectrum without proceeding complex sample pretreatment. 1D selective COSY reflects the more accurate position of hydrogen atom, and can be used as a reliable auxiliary technology for structural identification.},
     year = {2022}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - Analysis of the Alcohol Amine Mixtures by 1D Selective COSY
    AU  - Zhang He
    AU  - Huang Guilan
    AU  - Yang Hongyu
    Y1  - 2022/03/23
    PY  - 2022
    N1  - https://doi.org/10.11648/j.mc.20221001.12
    DO  - 10.11648/j.mc.20221001.12
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 5
    EP  - 11
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20221001.12
    AB  - Proton nuclear magnetic resonance (1H-NMR) is one of the most commonly used techniques for structure identification in the field of chemical warfare convention (CWC) because of its strong ability in aiding structure assignment of chemicals. However, due to the lack of separation function coupled with chromatograph, the greatest disadvantage of 1H-NMR in the analysis of environmental and biological samples is that the resonances can be easily covered or interfered. One-dimensional NMR selective excitation technology can effectively remove background interference and reveal the hidden spectral peak information. In this paper, three schedule chemicals of Chemical Weapons Convention (CWC), triethanolamine, N-methyldiethanolamine and 2-diisopropylaminoethanol, were selected as model chemicals. Homonuclear 1D COSY NMR selective excitation analysis method was established with these chemicals to solve the problem of resonances covered in 1H-NMR. Key experiment parameters of 1D COSY were optimized. The optimized experimental conditions of 1D COSY are as follows: pulse sequence is selcogp, shaped pulse is G3, relaxation delay of d1 is 4 s, the excitation width of dH 0.91 (a), 2.51 (g), 2.62 (e) and 3.44 (d) is 39.16, 35.34, 20.00 and 26.03 Hz respectively. The established 1D COSY method was used to analyze 1~10 μg/mL alcohol amine mixtures with 2 mg/mL quinuclidinol as the background interference and the LOD was 5 μg/mL. This method is simple, fast and can wipe off the interference effectively in the 1H NMR spectrum without proceeding complex sample pretreatment. 1D selective COSY reflects the more accurate position of hydrogen atom, and can be used as a reliable auxiliary technology for structural identification.
    VL  - 10
    IS  - 1
    ER  - 

    Copy | Download

Author Information
  • Department of Underwater Weaponry and Chemical Defense, Dalian Naval Academy, Dalian, China

  • State Key Laboratory of NBC Protection for Civilian, Institute of Chemical Defense, AMS, PLS, Beijing, China

  • Department of Underwater Weaponry and Chemical Defense, Dalian Naval Academy, Dalian, China

  • Sections