Citation: SUN Li-Li, ZHAO Yue-Hong, HAN Qing-Zhen, WEN Hao. Solvent Effect in the Reaction between Bis[1,2-di(trifluoromethyl) ethylene-1,2-dithiolato] Nickel and Butadiene[J]. Acta Physico-Chimica Sinica, ;2010, 26(12): 3345-3350. doi: 10.3866/PKU.WHXB20101225 shu

Solvent Effect in the Reaction between Bis[1,2-di(trifluoromethyl) ethylene-1,2-dithiolato] Nickel and Butadiene

1.
1. State Key Laboratory of Multiphase Complex System, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, P. R. China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received Date: 7 July 2010
Available Online: 10 November 2010
Fund Project: 国家自然科学基金(20703047, 20821092)资助项目 (20703047, 20821092)

We studied the reaction mechanism for the reaction between bis[1,2-di(trifluoromethyl) ethylene-1,2-dithiolato] nickel (Ni[S₂C₂(CF₃)₂]₂) and butadiene by density functional theory (DFT) at the B3LYP/6-31G(d) level. The solvent effect on the charge distribution, dipole moment, and solvation free energies of the stationary points were investigated using the polarizable continuum model (PCM). The calculation results showed that this reaction was orbital symmetry allowed and concerted. The reaction stationary points become more stable with an increase of solvent dielectric constant. Additionally, the degree of stabilization for the transition state and the product is larger than that of the reactants in the same solvent, which means that the reaction occurs more easily.
- Density functional theory,
- Bis[1,2-di(trifluoromethyl)ethylene-1,2-dithiolato] nickel,
- Butadiene,
- Solvent effect
1. [1]
  
  1. Wang, K.; Stiefel, E. I. Science, 2001, 291: 106
2. [2]
  2. Fan, Y. B.; Hall, M. B. J. Am. Chem. Soc., 2002, 124: 12076
3. [3]
  3. Harrison, D. J.; Nguyen, N.; Lough, A. J.; Fekl, U. J. Am. Chem. Soc., 2006, 128: 11026
4. [4]
  4. Szilagyi, R. K.; Lim, B. S.; Glaser, T.; Holm, R. H.; Hedman, B.; Hodgson, K. O.; Solomon, E. I. J. Am. Chem. Soc., 2003, 125: 9158
5. [5]
  5. Smith, R. S.; Herrera, P. S.; Henderson, J. F.; Spence, R. E. V. H. Selective chemical binding for olefins/paraffins separation. CA, 2415064
6. [6]
  [P]. 2004-06-23
7. [7]
  6. Field, M. J.; Bash, P. A.; Karplus, M. J. Comput. Chem., 1990, 11: 700
8. [8]
  7. Han, Q. Z.; Geng, C. Y.; Zhao, Y. H.; Qi, C. S.;Wen, H. Acta Phys. Sin., 2008, 57: 96
9. [9]
  [韩清珍; 耿春宇; 赵月红; 戚传松; 温浩. 物理学报, 2008, 57: 96]
10. [10]
  8. Han, Q. Z.; Zhao, Y. H.;Wen, H. Mol. Simulat., 2008, 34: 631
11. [11]
  9. Schrauze, G.; Ho, R. K. Y.; Murillo, R. P. J. Am. Chem. Soc., 1970, 92: 3508
12. [12]
  10. Baker, J. R.; Hermann, A.;Wing, R. M. J. Am. Chem. Soc., 1971, 93: 6486
13. [13]
  11. Clark, G. R.;Waters, J. M.;Whittle, K. R. J. Chem. Soc. Dalton Trans., 1973: 821
14. [14]
  12. Herman, A.;Wing, R. M. J. Organomet. Chem., 1973, 63: 441
15. [15]
  13. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett., 1996, 255: 327
16. [16]
  14. Barone, V.; Cossi, M. J. Phys. Chem. A, 1998, 102: 1995
17. [17]
  15. Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03. Revision A.01. Pittsburgh, PA: Gaussian Inc., 2003
18. [18]
  16. Hay, P. J.;Wadt,W. R. J. Chem. Phys., 1985, 82: 270
19. [19]
  17. Hay, P. J.;Wadt,W. R. J. Chem. Phys., 1985, 82: 299
20. [20]
  18. Couty, M.; Hall, M. B. J. Comput. Chem., 1996, 17: 1359
21. [21]
  19. Ehlers, A.W.; Bohme, M.; Dapprich, S.; bbi, A.; Hollwarth, A.; Jonas,V.; Kohler, K.F.; Stegmann, R.;Veldkamp,A.; Frenking, G. Chem. Phys. Lett., 1993, 208: 111
22. [22]
  20. Check, C. E.; Faust, T. O.; Bailey, J. M.;Wright, B. J.; Gilbert, T. M.; Sunderlin, L. S. J. Phys. Chem. A, 2001, 105: 8111
23. [23]
  21. Petersson, G. A.; Allaham, M. A. J. Chem. Phys., 1991, 94: 6081
24. [24]
  22. Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Allaham, M. A.; Shirley,W. A.; Mantzaris, J. J. Chem. Phys., 1988, 89: 2193
1. [1]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
2. [2]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
3. [3]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
4. [4]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
5. [5]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
6. [6]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
7. [7]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
8. [8]
  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
9. [9]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
10. [10]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
11. [11]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
12. [12]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
13. [13]
  Mengfei He , Chao Chen , Yue Tang , Si Meng , Zunfa Wang , Liyu Wang , Jiabao Xing , Xinyu Zhang , Jiahui Huang , Jiangbo Lu , Hongmei Jing , Xiangyu Liu , Hua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 100016-. doi: 10.3866/PKU.WHXB202310029
14. [14]
  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
15. [15]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
16. [16]
  Yaling Chen . Basic Theory and Competitive Exam Analysis of Dynamic Isotope Effect. University Chemistry, 2024, 39(8): 403-410. doi: 10.3866/PKU.DXHX202311093
17. [17]
  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
18. [18]
  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
19. [19]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
20. [20]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092

Get Citation

PDF

XML

Metrics

PDF Downloads(1136)
Abstract views(3338)
HTML views(6)

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