Citation: WU Pei-Ying, TZENG Sheng-Yuan, TSAI Ching-Yun, TZENG Wen-Bih. Rotamers of 2,5-Difluorophenol Studied Using Mass-Analyzed Threshold Ionization Spectroscopy[J]. Acta Physico-Chimica Sinica, ;2016, 32(4): 893-900. doi: 10.3866/PKU.WHXB201601293 shu

Rotamers of 2,5-Difluorophenol Studied Using Mass-Analyzed Threshold Ionization Spectroscopy

1.
1. Laboratory for Mass Spectrometric and Spectroscopic Studies of Biomolecules, Institute of Atomic and Molecular Sciences, Academia Sinica, Taipei 10617;
2.
2. Department of Chemistry, National Taiwan University, Taipei 10617;
3.
3. Department of Chemistry, National Taiwan Normal University, Taipei 11677

Corresponding author: TZENG Wen-Bih,
Received Date: 30 November 2015
Available Online: 28 January 2016
Fund Project: 国家科技部(MOST-103-2113-M-001-009, MOST-104-2113-M-001-014)资助项目 (MOST-103-2113-M-001-009, MOST-104-2113-M-001-014)

We applied resonant two-photon ionization (R²PI) and mass-analyzed threshold ionization (MATI) techniques to record the vibronic and cationic spectra of 2,5-difluorophenol. The distinct bands at 36448 and 36743 cm^-1 were confirmed as the origins of the S₁ ← S₀ electronic transition of the cis and trans rotamers, respectively. The corresponding adiabatic ionization energies were found to be 71164 and 71476 cm^-1 for these two rotameric species. The observed spectral features mainly result from the in-plane ring deformation and substituent-sensitive bending vibrations. Spectral analysis suggests that the molecular geometry and vibrational coordinates of the cation in the D₀ state resemble those of the neutral species in the S₁ state for both cis and trans rotamers.
- Resonant two-photon ionization technique,
- Threshold ionization,
- Vibronic spectrum,
- Cation spectrum,
- 2,5-Difluorophenol
1. [1]
  (1) Ribero da Silva, M. A. V.; Lobo Ferreira, A. I. M. C. J. Chem. Thermodyn. 2010, 42, 133. doi: 10.1016/j.jct.2009.07.021
2. [2]
  (2) Rao, R.; Aralakkanavar, M. K.; Rao, K. S.; Shashidhar, M. A. Spectrochim. Acta A 1989, 45, 103. doi: 10.1016/0584-8539(89)80110-2
3. [3]
  (3) Kolek, P.; Pirowska, K.; Gora, M.; Kozik, B.; Najbar, J. Chem. Phys. 2002, 285, 55. doi: 10.1016/S0301-0104(02)00689-4
4. [4]
  (4) Kolek, P.; Pirowska, K.; Chacaga, L.; Najbar, J. Phys. Chem. Chem. Phys. 2003, 5, 4096. doi: 10.1039/B305797F
5. [5]
  (5) Itoh, T.; Tanaka, N.; Tsukada, Y.; Nishikiori, H.; Fujii, T. J. Mol. Struct. 2011, 1000, 35. doi: 10.1016/j.molstruc.2011.05.046
6. [6]
  (6) Yoon, Y. K.; Huh, C. S.; Lee, S. K. Chem. Phys. Lett. 2012, 550, 58. doi: 10.1016/j.cplett.2012.08.060
7. [7]
  (7) Huh, C. S.; Yoon, Y.W.; Lee, S. K. J. Chem. Phys. 2012, 136, 174306. doi: 10.1063/1.4708808
8. [8]
  (8) Ito, M.; Oikawa, A. J. Mol. Struct. 1985, 126, 133. doi: 10.1016/0022-2860(85) 80109-5
9. [9]
  (9) Kazmierski, W. M.; Danehower, S.; Duan, M.; Ferris, R. G.; Elitzin, V.; Minick, D.; Sharp, M.; Stewart, E.; Villeneuve, M.; Med. Chem. Lett. 2014, 5, 1296. doi: 10.1021/ml5004124
10. [10]
  (10) Ortega, D. R.; Yang, C.; Ames, P.; Baudry, J.; Parkinson, J. S.; Zhulin, I. B. Nat. Commun. 2013, 4, 1. doi: 1038/ncomms3881
11. [11]
  (11) Chakrabarti, S.; Jaman, A. I. J. Mol. Struct. 2002, 642, 93. doi: 10.1016/S0022-2860(02) 00398-8
12. [12]
  (12) Shivatare, V.; Tzeng, W. B. Bull. Korean Chem. Soc. 2014, 35, 815. doi: 10.5012/bkcs.2014.35.3.815
13. [13]
  (13) Tsai, C. Y.; Tzeng, W. B. J. Photochem. Photobiol. A 2013, 270, 53. doi: 10.1016/j.jphotochem.2013.07.014
14. [14]
  (14) Fujii, A.; Iwasaki, A.; Mikami, N. Chem. Lett. 1997, 11, 1099. doi: 10.1246/cl.1997.1099
15. [15]
  (15) Fujimaki, E.; Fujii, A.; Ebata, T.; Mikami, N. J. Chem. Phys. 1999, 110, 4238. doi: 10.1063/1.478306
16. [16]
  (16) Yuan, L.; Li, C.; Lin, J. L.; Yang, S. C.; Tzeng, W. B. Chem. Phys. 2006, 323, 429. doi: 10.1016/j.chemphys.2005.10.004
17. [17]
  (17) Oikawa, A.; Abe, H.; Mikami, N.; Ito, M. Chem. Phys. Lett. 1985, 116, 50. doi: 10.1016/0009-2614(85) 80123-8
18. [18]
  (18) Yosida, K.; Suzuki, K.; Ishiuchi, S.; Sakai, M.; Fujii, M.; Dessent, C. E. H.; Muller-Dethlefs, K. Phys. Chem. Chem. Phys. 2002, 4, 2534. doi: 10.1039/B201107G
19. [19]
  (19) Zhang, B.; Li, C.; Su, H.; Lin, J. L.; Tzeng, W. B. Chem. Phys. Lett. 2004, 390, 65. doi: 10.1016/j.cplett.2004.04.013
20. [20]
  (20) Huang, W. C.; Huang, P. S.; Hu, C. H.; Tzeng, W. B. Chem. Phys. Lett. 2013, 580, 28. doi: 10.1016/j.cplett.2013.06.053
21. [21]
  (21) Ribeiro-Claro, P. J. A.; Teixeira-Dias, J. J. C.; Hollas, J. M.; Milewski, M. J. Chem. Soc. Faraday Trans. 1995, 91, 197. doi: 10.1039/FT9959100197
22. [22]
  (22) Breen, P. J.; Bernstein, E. R.; Secor, H. V.; Seeman, J. I. J. Am. Chem. Soc. 1989, 111, 1958. doi: 10.1021/ja00188a002
23. [23]
  (23) Li, C.; Lin, J. L.; Tzeng, W. B. J. Chem. Phys. 2005, 122, 044311. doi: 10.1063/1.1839863
24. [24]
  (24) Gerhards, M.; Perl, W.; Kleinermanns, K. Chem. Phys. Lett. 1995, 240, 506. doi: 10.1016/0009-2614(95) 00567-N
25. [25]
  (25) Patwari, G. N.; Doraiswamy, S.;Wategaonkar, S. Chem. Phys. Lett. 1998, 289, 8. doi: 10.1016/S0009-2614(98)00398-4
26. [26]
  (26) Telle, H. H.; Urena, A. G.; Donovan, R. J. Laser Chemistry; JohnWiley & Sons, Ltd.:West Sussex, England, 2007.
27. [27]
  (27) Müller-Dethlefs, K.; Sander, K. M.; Schlag, E.W. Chem. Phys. Lett. 1984, 112, 291. doi: 10.1016/0009-2614(84)85743-7
28. [28]
  (28) Müller-Dethlefs, K.; Dopfer, O.;Wright, T. G. Chem. Rev. 1994, 94, 1845. doi: 10.1021/cr00031a006
29. [29]
  (29) Cockett, M. C. R. Chem. Soc. Rev. 2005, 34, 935. doi: 10.1039/b505794a
30. [30]
  (30) Zhu, L.; Johnson, P. J. Chem. Phys. 1991, 94, 5769. doi: 10.1063/1.460460
31. [31]
  (31) Dessent, C. E. H.; Haines, S.; Müller-Dethlefs, K. Chem. Phys. Lett. 1999, 315, 103. doi: 10.1016/S0009-2614(99)01193-8
32. [32]
  (32) Georgiev, S.; Karaminkov, R.; Chervenkov, S.; Delchev, V.; Neusser, H. J. J. Phys. Chem. A 2009, 113, 12328. doi: 10.1021/jp908045k
33. [33]
  (33) Witte, F.; Riese, M.; Gunzer, F.; Grotemeyer, J. Int. J. Mass Spectrom. 2011, 306, 129. doi: 10.1016/j.ijms.2010.10.002
34. [34]
  (34) Lin, J. L.; Tzeng, W. B. Appl. Spectrosc. 2003, 57, 1178. doi: 10.1366/00037020360696062
35. [35]
  (35) Xu, Y.; Tzeng, S. Y.; Shivatare, V.; Takahashi, K.; Zhang, B.; Tzeng, W. B. J. Chem. Phys. 2015, 142, 124314. doi: 10.1063/1.4916052
36. [36]
  (36) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.02; Gaussian Inc.:Wallingford, CT, 2009.
37. [37]
  (37) Dennington, R.; Keith, T.; Millam, J.; GaussView, Version 5; Semichem Inc. :Shawnee Mission KS, 2009.
38. [38]
  (38) Varsanyi, G.; Szoke, S. Vibrational Spectra of Benzene Derivatives; Academic Press: London, 1969.
39. [39]
  (39) Varsanyi, G. Assignments of Vibrational Spectra of Seven Hundred Benzene Derivatives;Wiley: New York, 1974.
40. [40]
  (40) Wilson, E. B. Phys. Rev. 1934, 45, 406. doi: 10.1103/PhysRev.45.706
41. [41]
  (41) Shinozaki, M.; Sakai, M.; Yamaguchi, S.; Fujioka, T.; Fujii, M. Phys. Chem. Chem. Phys. 2003, 5, 5044. doi: 10.1039/B309461H
42. [42]
  (42) Dopfer, O.; Müller-Dethlefs, K. J. Chem. Phys. 1994, 101, 8508. doi: 10.1063/1.468111
43. [43]
  (43) Wu, P. Y.; Tzeng, W. B. J. Mol. Spectrosc. 2015, 316, 72. doi: 10.1016/j.jms.2015.06.011
44. [44]
  (44) Shiung, K. S.; Yu, D.; Huang, H. C.; Tzeng, W. B. J. Mol. Spectrosc. 2012, 274, 43. doi: 10.1016/j.jms.2012.04.004
45. [45]
  (45) Xu, Y.; Tzeng, S. Y.; Zhang, B.; Tzeng, W. B. Spectrochim. Acta A 2013, 102, 365. doi: 10.1016/j.saa.2012.10.020
1. [1]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
2. [2]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
3. [3]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
4. [4]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
5. [5]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
6. [6]
  Zhuomin Zhang , Hanbing Huang , Liangqiu Lin , Jingsong Liu , Gongke Li . Course Construction of Instrumental Analysis Experiment: Surface-Enhanced Raman Spectroscopy for Rapid Detection of Edible Pigments. University Chemistry, 2024, 39(2): 133-139. doi: 10.3866/PKU.DXHX202308034
7. [7]
  Jingyi Chen , Fu Liu , Tiejun Zhu , Kui Cheng . Practice of Integrating Ideological and Political Education into Raman Spectroscopy Analysis Experiment Course. University Chemistry, 2024, 39(2): 140-146. doi: 10.3866/PKU.DXHX202310111
8. [8]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
9. [9]
  Tianlong Zhang , Jiajun Zhou , Hongsheng Tang , Xiaohui Ning , Yan Li , Hua Li . Virtual Simulation Experiment for Laser-Induced Breakdown Spectroscopy (LIBS) Analysis. University Chemistry, 2024, 39(6): 295-302. doi: 10.3866/PKU.DXHX202312049
10. [10]
  Wei Peng , Baoying Wen , Huamin Li , Yiru Wang , Jianfeng Li . Exploration and Practice on Raman Scattering Spectroscopy Experimental Teaching. University Chemistry, 2024, 39(8): 230-240. doi: 10.3866/PKU.DXHX202312062
11. [11]
  Zhaoyue Lü , Zhehao Chen , Yi Ni , Duanbin Luo , Xianfeng Hong . Multi-Level Teaching Design and Practice Exploration of Raman Spectroscopy Experiment. University Chemistry, 2024, 39(11): 304-312. doi: 10.12461/PKU.DXHX202402047
12. [12]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
13. [13]
  Mengyao Shi , Kangle Su , Qingming Lu , Bin Zhang , Xiaowen Xu . Determination of Potassium Content in Tobacco Stem Ash by Flame Atomic Absorption Spectroscopy. University Chemistry, 2024, 39(10): 255-260. doi: 10.12461/PKU.DXHX202404105
14. [14]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
15. [15]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
16. [16]
  Siyu Zhang , Kunhong Gu , Bing'an Lu , Junwei Han , Jiang Zhou . Hydrometallurgical Processes on Recycling of Spent Lithium-lon Battery Cathode: Advances and Applications in Sustainable Technologies. Acta Physico-Chimica Sinica, 2024, 40(10): 2309028-. doi: 10.3866/PKU.WHXB202309028
17. [17]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
18. [18]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
19. [19]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
20. [20]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(248)
HTML views(28)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142