Citation: Ren Yi, Liu Qing-Yu, Zhao Yan-Xia, Yang Qi, He Sheng-Gui. C―C Coupling of Methane Mediated by Atomic Gold Cations under Multiple-Collision Conditions[J]. Acta Physico-Chimica Sinica, ;2020, 36(1): 190402. doi: 10.3866/PKU.WHXB201904026 shu

C―C Coupling of Methane Mediated by Atomic Gold Cations under Multiple-Collision Conditions

Ren Yi ^1,2,3,4 ,
Liu Qing-Yu ^1,3,4,, ,
Zhao Yan-Xia ^1,3,4 ,
Yang Qi ^1,3,4 ,
He Sheng-Gui ^1,2,3,4,,

1.
State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
2.
University of Chinese Academy of Sciences, Beijing 100049, P. R. China
3.
Beijing National Laboratory for Molecular Sciences, Beijing 100190, P. R. China
4.
CAS Research/Education Center of Excellence in Molecular Sciences, Beijing 100190, P. R. China

Corresponding author: Liu Qing-Yu, liuqingyu12@iccas.ac.cn He Sheng-Gui, shengguihe@iccas.ac.cn
Received Date: 8 April 2019
Revised Date: 25 April 2019
Accepted Date: 25 April 2019
Available Online: 29 January 2019
Fund Project: the National Key Research and Development Program of China 2017YFC0209403the Youth Innovation Promotion Association, Chinese Academy of Sciences 2018041The project was supported by the National Natural Science Foundation of China (21627803, 91645203) and the National Key Research and Development Program of China (2017YFC0209403). Y. -X. Zhao thanks the grant from the Youth Innovation Promotion Association, Chinese Academy of Sciences (2018041)the National Natural Science Foundation of China 21627803the National Natural Science Foundation of China 91645203

The reactivity of atomic metal cations toward CH₄ has been extensively investigated over the past decades. Closed-shell metal cations in electronically ground states are usually inert with CH₄ under thermal collision conditions because of the extremely high stability of methane. With the elevation of collision energies, closed-shell atomic gold cations (Au⁺) have been reported to react with CH₄ under single-collision conditions to produce AuCH₂⁺, AuH⁺, and AuCH₃⁺ species. Further investigations found that the ion-source-generated AuCH₂⁺ cations can react with CH₄ to synthesize C―C coupling products. These previous studies suggested that new products for the reaction of Au⁺ with CH₄ can be identified under multiple-collision conditions with sufficient collision energies. However, the reported ion-molecule reactions involving methane were usually performed under single- or multiple-collision conditions with thermal collision energies. In this study, a new reactor composed of a drift tube and ion funnel is constructed and coupled with a homemade reflectron time-of-flight mass spectrometer. Laser-ablation-generated Au⁺ ions are injected into the reactor and drift 120 mm to react with methane seeded in the helium drift gas. The reaction products and unreacted Au⁺ ions are focused through the ion funnel and accumulate through a linear ion trap and are then detected by a mass spectrometer. In the reactor, the pressure is approximately 100 Pa, and the electric field between the drift tube and ion funnel can regulate the collision energies between ions and molecules. The reaction of the closed-shell atomic Au⁺ cation with CH₄ is investigated, and the C―C coupling product AuC₂H₄⁺ is observed under multiple-collision conditions with elevated collision energies. Density functional theory calculations are performed to understand the mechanism of the coupling reaction (Au⁺+ 2CH₄ → AuC₂H₄⁺ + 2H₂). Two pathways involving Au―CH₂ and Au―CH₃ species can separately mediate the C―C coupling process. The activation of the second C―H bond in each process requires additional energy to overcome the relatively high barrier (2.07 and 2.29 eV). Ion-trajectory simulations under multiple-collision conditions are then conducted to determine the collisional energy distribution in the reactor. These simulations confirmed that the electric fields between the drift tube and ion funnel could supply sufficient center-of-mass kinetic energies to facilitate the C―C coupling process to form AuC₂H₄⁺. The following catalytic cycle could then be postulated: \begin{document}$\mathrm{AuC}_{2} \mathrm{H}_{4}^{+}+\mathrm{CH}_{4} \stackrel{\Delta}{\longrightarrow} \mathrm{AuCH}_{4}^{+}+\mathrm{C}_{2} \mathrm{H}_{4}, \mathrm{AuCH}_{4}^{+}+\mathrm{CH}_{4} \stackrel{\Delta}{\longrightarrow} \mathrm{AuC}_{2} \mathrm{H}_{4}^{+}+2 \mathrm{H}_{2}$\end{document}, and \begin{document}$\mathrm{CH}_{4} \stackrel{\mathrm{Au}^{+}, \Delta}{\longrightarrow} \mathrm{C}_{2} \mathrm{H}_{4}+2 \mathrm{H}_{2}$\end{document}. Thus, this study enriches the chemistry of both gold and methane.
- Gold,
- Methane,
- Ion-molecule reaction,
- C―C coupling,
- Mass spectrometry
1. [1]
  Lunsford, J. H. Catal. Today 2000, 63, 165. doi: 10.1016/s0920-5861(00)00456-9 doi: 10.1016/s0920-5861(00)00456-9
2. [2]
  Caballero, A.; Pérez, P. J. Chem. Soc. Rev. 2013, 42, 8809. doi: 10.1039/c3cs60120j doi: 10.1039/c3cs60120j
3. [3]
  Saha, D.; Grappe, H. A.; Chakraborty, A.; Orkoulas, G. Chem. Rev. 2016, 116, 11436. doi: 10.1021/acs.chemrev.5b00745 doi: 10.1021/acs.chemrev.5b00745
4. [4]
  Ismagilov, Z. R.; Matus, E. V.; Tsikoza, L. T. Energy Environ. Sci. 2008, 1, 526. doi: 10.1039/b810981h doi: 10.1039/b810981h
5. [5]
  Spivey, J. J.; Hutchings, G. Chem. Soc. Rev. 2014, 43, 792. doi: 10.1039/c3cs60259a doi: 10.1039/c3cs60259a
6. [6]
  Schwach, P.; Pan, X.; Bao, X. Chem. Rev. 2017, 117, 8497. doi: 10.1021/acs.chemrev.6b00715 doi: 10.1021/acs.chemrev.6b00715
7. [7]
  Schwarz, H.; González-Navarrete, P.; Li, J.; Schlangen, M.; Sun, X.; Weiske, T.; Zhou, S. Organometallics 2017, 36, 8. doi: 10.1021/acs.organomet.6b00372 doi: 10.1021/acs.organomet.6b00372
8. [8]
  Ding, X. -L.; Wu, X. -N.; Zhao, Y. -X.; He, S. -G. Acc. Chem. Res. 2012, 45, 382. doi: 10.1021/ar2001364 doi: 10.1021/ar2001364
9. [9]
  Feyel, S.; Döbler, J.; Schröder, D.; Sauer, J.; Schwarz, H. Angew. Chem. Int. Ed. 2006, 45, 4681. doi: 10.1002/anie.200600188 doi: 10.1002/anie.200600188
10. [10]
  Harding, D. J.; Kerpal, C.; Meijer, G.; Fielicke, A. Angew. Chem. Int. Ed. 2012, 51, 817. doi: 10.1002/anie.201107042 doi: 10.1002/anie.201107042
11. [11]
  Lang, S. M.; Frank, A.; Bernhardt, T. M. J. Phys. Chem. C 2013, 117, 9791. doi: 10.1021/jp312852r doi: 10.1021/jp312852r
12. [12]
  Canale, V.; Zavras, A.; Khairallah, G. N.; d'Alessandro, N.; O'Hair, R. A. J. Eur. J. Mass Spectrom. 2015, 21, 557. doi: 10.1255/ejms.1332 doi: 10.1255/ejms.1332
13. [13]
  Lang, S. M.; Bernhardt, T. M.; Chernyy, V.; Bakker, J. M.; Barnett, R. N.; Landman, U. Angew. Chem. Int. Ed. 2017, 56, 13406. doi: 10.1002/anie.201706009 doi: 10.1002/anie.201706009
14. [14]
  Caballero, A.; Despagnet-Ayoub, E.; Díaz-Requejo, M. M.; Díaz-Rodríguez, A.; González-Núñez, M. E.; Mello, R.; Muñoz, B. K.; Ojo, W. S.; Asensio, G.; Etienne, M.; et al. Science 2011, 332, 835. doi: 10.1126/science.1204131 doi: 10.1126/science.1204131
15. [15]
  Guo, X.; Fang, G.; Li, G.; Ma, H.; Fan, H.; Yu, L.; Ma, C.; Wu, X.; Deng, D.; Wei, M.; et al. Science 2014, 344, 616. doi: 10.1126/science.1253150 doi: 10.1126/science.1253150
16. [16]
  Sushkevich, V. L.; Palagin, D.; Ranocchiari, M.; van Bokhoven, J. A. Science 2017, 356, 523. doi: 10.1126/science.aam9035 doi: 10.1126/science.aam9035
17. [17]
  Tonkyn, R.; Ronan, M.; Weisshaar, J. C. J. Phys. Chem. 1988, 92, 92. doi: 10.1021/j100312a022 doi: 10.1021/j100312a022
18. [18]
  Irikura, K. K.; Beauchamp, J. L. J. Phys. Chem. 1991, 95, 8344. doi: 10.1021/j100174a057 doi: 10.1021/j100174a057
19. [19]
  Irikura, K. K.; Beauchamp, J. L. J. Am. Chem. Soc. 1991, 113, 2769. doi: 10.1021/ja00007a070 doi: 10.1021/ja00007a070
20. [20]
  Cornehl, H. H.; Heinemann, C.; Schröder, D.; Schwarz, H. Organometallics 1995, 14, 992. doi: 10.1021/om00002a053 doi: 10.1021/om00002a053
21. [21]
  Schwarz, H.; Schröder, D. Pure Appl. Chem. 2000, 72, 2319. doi: 10.1351/pac200072122319 doi: 10.1351/pac200072122319
22. [22]
  Shayesteh, A.; Lavrov, V. V.; Koyanagi, G. K.; Bohme, D. K. J. Phys. Chem. A 2009, 113, 5602. doi: 10.1021/jp900671c doi: 10.1021/jp900671c
23. [23]
  van Koppen, P. A. M.; Kemper, P. R.; Bushnell, J. E.; Bowers, M. T. J. Am. Chem. Soc. 1995, 117, 2098. doi: 10.1021/ja00112a026 doi: 10.1021/ja00112a026
24. [24]
  Sunderlin, L. S.; Armentrout, P. B. J. Am. Chem. Soc. 1989, 111, 3845. doi: 10.1021/ja00193a015 doi: 10.1021/ja00193a015
25. [25]
  Haynes, C. L.; Chen, Y.-M.; Armentrout, P. B. J. Phys. Chem. 1995, 99, 9110. doi: 10.1021/j100022a024 doi: 10.1021/j100022a024
26. [26]
  Armentrout, P. B.; Chen, Y.-M. Int. J. Mass Spectrom. 2017, 413, 135. doi: 10.1016/j.ijms.2016.05.003 doi: 10.1016/j.ijms.2016.05.003
27. [27]
  Li, F.-X.; Armentrout, P. B. J. Chem. Phys. 2006, 125, 133114. doi: 10.1063/1.2220038 doi: 10.1063/1.2220038
28. [28]
  Zhou, S.; Li, J.; Wu, X.-N.; Schlangen, M.; Schwarz, H. Angew. Chem. Int. Ed. 2016, 55, 441. doi: 10.1002/anie.201509320 doi: 10.1002/anie.201509320
29. [29]
  Karakaya, C.; Kee, R. J. Prog. Energy Combust. Sci. 2016, 55, 60. doi: 10.1016/j.pecs.2016.04.003 doi: 10.1016/j.pecs.2016.04.003
30. [30]
  Tomkins, P.; Ranocchiari, M.; van Bokhoven, J. A. Acc. Chem. Res. 2017, 50, 418. doi: 10.1021/acs.accounts.6b00534 doi: 10.1021/acs.accounts.6b00534
31. [31]
  Sun, K.; Ginosar, D. M.; He, T.; Zhang, Y.; Fan, M.; Chen, R. Ind. Eng. Chem. Res. 2018, 57, 1768. doi: 10.1021/acs.iecr.7b04707 doi: 10.1021/acs.iecr.7b04707
32. [32]
  Geusic, M. E.; Morse, M. D.; O'Brien, S. C.; Smalley, R. E. Rev. Sci. Instrum. 1985, 56, 2123. doi: 10.1063/1.1138381 doi: 10.1063/1.1138381
33. [33]
  Smith, D.; Španěl, P. Mass Spectrom. Rev. 2005, 24, 661. doi: 10.1002/mas.20033 doi: 10.1002/mas.20033
34. [34]
  Melko, J. J.; Ard, S. G.; Shuman, N. S.; Pedder, R. E.; Taormina, C. R.; Viggiano, A. A. Rev. Sci. Instrum. 2015, 86, 084101. doi: 10.1063/1.4927716 doi: 10.1063/1.4927716
35. [35]
  McDonald, D. C.; Sweeny, B. C.; Ard, S. G.; Melko, J. J.; Ruliffson, J. E.; White, M. C.; Viggiano, A. A.; Shuman, N. S. J. Phys. Chem. A 2018, 122, 6655. doi: 10.1021/acs.jpca.8b02513 doi: 10.1021/acs.jpca.8b02513
36. [36]
  Gronert, S. Mass Spectrom. Rev. 2005, 24, 100. doi: 10.1002/mas.20008 doi: 10.1002/mas.20008
37. [37]
  Douglas, D. J.; Frank, A. J.; Mao, D. Mass Spectrom. Rev. 2005, 24, 1. doi: 10.1002/mas.20004 doi: 10.1002/mas.20004
38. [38]
  Nibbering, N. M. M. Acc. Chem. Res. 1990, 23, 279. doi: 10.1021/ar00177a003 doi: 10.1021/ar00177a003
39. [39]
  Teloy, E.; Gerlich, D. Chem. Phys. 1974, 4, 417. doi: 10.1016/0301-0104(74)85008-1 doi: 10.1016/0301-0104(74)85008-1
40. [40]
  Armentrout, P. B.; Beauchamp, J. L. Acc. Chem. Res. 1989, 22, 315. doi: 10.1021/ar00165a004 doi: 10.1021/ar00165a004
41. [41]
  May, J. C.; McLean, J. A. Anal. Chem. 2015, 87, 1422. doi: 10.1021/ac504720m doi: 10.1021/ac504720m
42. [42]
  Lanucara, F.; Holman, S. W.; Gray, C. J.; Eyers, C. E. Nat. Chem. 2014, 6, 281. doi: 10.1038/nchem.1889 doi: 10.1038/nchem.1889
43. [43]
  Zhan, X.; Duan, J.; Duan, Y. Mass Spectrom. Rev. 2013, 32, 143. doi: 10.1002/mas.21357 doi: 10.1002/mas.21357
44. [44]
  Yuan, B.; Koss, A. R.; Warneke, C.; Coggon, M.; Sekimoto, K.; de Gouw, J. A. Chem. Rev. 2017, 117, 13187. doi: 10.1021/acs.chemrev.7b00325 doi: 10.1021/acs.chemrev.7b00325
45. [45]
  Kučera, M.; Stano, M.; Wnorowska, J.; Barszczewska, W.; Loffhagen, D.; Matejčík, Š. Eur. Phys. J. D 2013, 67, 234. doi: 10.1140/epjd/e2013-40401-2 doi: 10.1140/epjd/e2013-40401-2
46. [46]
  Gao, H.; Niu, W.; Huang, C.; Hong, Y.; Shen, C.; Wang, H.; Lu, Y.; Chen, X.; Xia, L.; Jiang, H.; Chu, Y. Int. J. Mass spectrom. 2015, 376, 1. doi: 10.1016/j.ijms.2014.11.001 doi: 10.1016/j.ijms.2014.11.001
47. [47]
  Kemper, P. R.; Bowers, M. T. J. Am. Soc. Mass. Spectrom. 1990, 1, 197. doi: 10.1016/1044-0305(90)85036-l doi: 10.1016/1044-0305(90)85036-l
48. [48]
  Backe, H.; Dretzke, A.; Horn, R.; Kolb, T.; Lauth, W.; Repnow, R.; Sewtz, M.; Trautmann, N. Hyperfine Interact. 2006, 162, 77. doi: 10.1007/s10751-005-9210-4 doi: 10.1007/s10751-005-9210-4
49. [49]
  Wyttenbach, T.; Kemper, P. R.; Bowers, M. T. Int. J. Mass Spectrom. 2001, 212, 13. doi: 10.1016/s1387-3806(01)00517-6 doi: 10.1016/s1387-3806(01)00517-6
50. [50]
  Tang, K.; Shvartsburg, A. A.; Lee, H. N.; Prior, D. C.; Buschbach, M. A.; Li, F.; Tolmachev, A. V.; Anderson, G. A.; Smith, R. D. Anal. Chem. 2005, 77, 3330. doi: 10.1021/ac048315a doi: 10.1021/ac048315a
51. [51]
  Koeniger, S. L.; Merenbloom, S. I.; Valentine, S. J.; Jarrold, M. F.; Udseth, H. R.; Smith, R. D.; Clemmer, D. E. Anal. Chem. 2006, 78, 4161. doi: 10.1021/ac051060w doi: 10.1021/ac051060w
52. [52]
  Kelly, R. T.; Tolmachev, A. V.; Page, J. S.; Tang, K.; Smith, R. D. Mass Spectrom. Rev. 2010, 29, 294. doi: 10.1002/mas.20232 doi: 10.1002/mas.20232
53. [53]
  Shi, L.; Holliday, A. E.; Bohrer, B. C.; Kim, D.; Servage, K. A.; Russell, D. H.; Clemmer, D. E. J. Am. Soc. Mass. Spectrom. 2016, 27, 1037. doi: 10.1007/s13361-016-1372-6 doi: 10.1007/s13361-016-1372-6
54. [54]
  Wagner, N. D.; Clemmer, D. E.; Russell, D. H. Anal. Chem. 2017, 89, 10094. doi: 10.1021/acs.analchem.7b02932 doi: 10.1021/acs.analchem.7b02932
55. [55]
  Yuan, Z.; Liu, Q. -Y.; Li, X. -N.; He, S. -G. Int. J. Mass Spectrom. 2016, 407, 62. doi: 10.1016/j.ijms.2016.07.004 doi: 10.1016/j.ijms.2016.07.004
56. [56]
  Li, F. -X.; Gorham, K.; Armentrout, P. B. J. Phys. Chem. A 2010, 114, 11043. doi: 10.1021/jp100566t doi: 10.1021/jp100566t
57. [57]
  Zhao, Y. X.; Li, Z. Y.; Yuan, Z.; Li, X. N.; He, S. G. Angew. Chem. Int. Ed. 2014, 53, 9482. doi: 10.1002/anie.201403953 doi: 10.1002/anie.201403953
58. [58]
  Yuan, Z.; Li, Z. -Y.; Zhou, Z. -X.; Liu, Q. -Y.; Zhao, Y. -X.; He, S. -G. J. Phys. Chem. C 2014, 118, 14967. doi: 10.1021/jp5040344 doi: 10.1021/jp5040344
59. [59]
  SIMION® Version 8.1. Scientific Instrument Services, Inc.^TM 2011.
60. [60]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision A.01; Gaussian Inc.: Wallingford, CT, USA, 2009.
61. [61]
  Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401. doi: 10.1103/PhysRevLett.91.146401 doi: 10.1103/PhysRevLett.91.146401
62. [62]
  Li, Z. -Y.; Li, H. -F.; Zhao, Y. -X.; He, S. -G. J. Am. Chem. Soc. 2016, 138, 9437. doi: 10.1021/jacs.6b03940 doi: 10.1021/jacs.6b03940
63. [63]
  Meng, J. -H.; He, S. -G. J. Phys. Chem. Lett. 2014, 5, 3890. doi: 10.1021/jz502057n doi: 10.1021/jz502057n
64. [64]
  Kanai, Y.; Wang, X.; Selloni, A.; Car, R. J. Chem. Phys. 2006, 125, 234104. doi: 10.1063/1.2403861 doi: 10.1063/1.2403861
65. [65]
  Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. doi: 10.1063/1.438955 doi: 10.1063/1.438955
66. [66]
  Andrae, D.; Häuϐermann, U.; Dolg, M.; Stoll, H.; Preuϐ, H. Theor. Chim. Acta 1990, 77, 123. doi: 10.1007/bf01114537 doi: 10.1007/bf01114537
67. [67]
  Schlegel, H. B. J. Comput. Chem. 1982, 3, 214. doi: 10.1002/jcc.540030212 doi: 10.1002/jcc.540030212
68. [68]
  Berente, I.; Náray-Szabó, G. J. Phys. Chem. A 2006, 110, 772. doi: 10.1021/jp054116z doi: 10.1021/jp054116z
69. [69]
  Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154. doi: 10.1063/1.456010 doi: 10.1063/1.456010
70. [70]
  Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523. doi: 10.1021/j100377a021 doi: 10.1021/j100377a021
71. [71]
  Zhang, T.; Li, Z. -Y.; Zhang, M. -Q.; He, S. -G. J. Phys. Chem. A 2016, 120, 4285. doi: 10.1021/acs.jpca.6b03836 doi: 10.1021/acs.jpca.6b03836
72. [72]
  Lang, S. M.; Bernhardt, T. M.; Barnett, R. N.; Landman, U. Angew. Chem. Int. Ed. 2010, 49, 980. doi: 10.1002/anie.200905643 doi: 10.1002/anie.200905643
1. [1]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
2. [2]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
3. [3]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
4. [4]
  Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
5. [5]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
6. [6]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
7. [7]
  Keqiang Shi , Xiujuan Hong , Dongyan Xu , Tao Pan , Huiwen Wang , Hongru Feng , Cheng Guo , Yuanjiang Pan . Analysis of RNA modifications in peripheral white blood cells from breast cancer patients by mass spectrometry. Chinese Chemical Letters, 2025, 36(3): 110079-. doi: 10.1016/j.cclet.2024.110079
8. [8]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
9. [9]
  Yao-Hua Gu , Yu Chen , Qing Li , Neng-Bin Xie , Xue Xing , Jun Xiong , Min Hu , Tian-Zhou Li , Ke-Yu Yuan , Yu Liu , Tang Tang , Fan He , Bi-Feng Yuan . Metabolome profiling by widely-targeted metabolomics and biomarker panel selection using machine-learning for patients in different stages of chronic kidney disease. Chinese Chemical Letters, 2024, 35(11): 109627-. doi: 10.1016/j.cclet.2024.109627
10. [10]
  Lu Huang , Jiang Wang , Hong Jiang , Lanfang Chen , Huanwen Chen . On-line determination of selenium compounds in tea infusion by extractive electrospray ionization mass spectrometry combined with a heating reaction device. Chinese Chemical Letters, 2025, 36(1): 109896-. doi: 10.1016/j.cclet.2024.109896
11. [11]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
12. [12]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
13. [13]
  Wei Shao , Wanqun Zhang , Pingping Zhu , Wanqun Hu , Qiang Zhou , Weiwei Li , Kaiping Yang , Xisheng Wang . Design and Practice of Ideological and Political Cases in the Course of Instrument Analysis Experiment: Taking the GC-MS Experiment as an Example. University Chemistry, 2024, 39(2): 147-154. doi: 10.3866/PKU.DXHX202309048
14. [14]
  Yanhua Chen , Xian Ding , Jun Zhou , Zhaoying Wang , Yunhai Bo , Ying Hu , Qingce Zang , Jing Xu , Ruiping Zhang , Jiuming He , Fen Yang , Zeper Abliz . Plasma metabolomics combined with mass spectrometry imaging reveals crosstalk between tumor and plasma in gastric cancer genesis and metastasis. Chinese Chemical Letters, 2025, 36(1): 110351-. doi: 10.1016/j.cclet.2024.110351
15. [15]
  Haiyan Lu , Jiayue Ye , Yiping Wei , Hua Zhang , Konstantin Chingin , Vladimir Frankevich , Huanwen Chen . Tracing molecular margins of lung cancer by internal extractive electrospray ionization mass spectrometry. Chinese Chemical Letters, 2025, 36(2): 110077-. doi: 10.1016/j.cclet.2024.110077
16. [16]
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20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142