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]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
5. [5]
  Yuai Duan , Xuanyu Gan , Yao Fu , Yingjie Cao , Hongliang Han , Zhanfang Ma . Application and Innovative Design of Digital Technology in the Preparation Experiment of Cis(Trans)-Diglycine Copper Complexes. University Chemistry, 2026, 41(1): 373-381. doi: 10.12461/PKU.DXHX202504048
6. [6]
  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): 100012-0. doi: 10.3866/PKU.WHXB202309027
7. [7]
  Mengfan Gong , Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036
8. [8]
  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
9. [9]
  Yupeng TANG , Haiying YANG , Fan JIN , Nan LI . Hydrogen storage properties of C₆S₆Li₆: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1827-1839. doi: 10.11862/CJIC.20240460
10. [10]
  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
11. [11]
  Chenxu Gong , Weizhen Wang , Ruiying Zhang , Wenfeng Wang , Yuanming Li , Yaofeng Yuan , Keyin Ye . Computational Chemistry-Assisted Organic Structure Analysis (CCAOSA): A Case Study of Propeller-Shaped Hexabenzotriphenylene. University Chemistry, 2026, 41(4): 438-446. doi: 10.12461/PKU.DXHX202503076
12. [12]
  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
13. [13]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
14. [14]
  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
15. [15]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
16. [16]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
17. [17]
  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
18. [18]
  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
19. [19]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429
20. [20]
  Tongqi Ye , Yanqing Wang , Qi Wang , Huaiping Cong , Xianghua Kong , Yuewen Ye . Reform of Classical Thermodynamics Curriculum from the Perspective of Computational Chemistry. University Chemistry, 2025, 40(7): 387-392. doi: 10.12461/PKU.DXHX202409128

Get Citation

PDF

XML

Metrics

PDF Downloads(1136)
Abstract views(3901)
HTML views(32)

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