Citation: Li Qianggen, Xiang Shikai, Mao Shuang, Ren Yi. Theoretical Investigations on the Intramolecular N-Arylation Mechanism and Reactivity for the Synthesis of Benzimidazoles by Base-Catalyzed[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 608-616. doi: 10.6023/cjoc201609020 shu

Theoretical Investigations on the Intramolecular N-Arylation Mechanism and Reactivity for the Synthesis of Benzimidazoles by Base-Catalyzed

Li Qianggen ^a,*,, ,
Xiang Shikai ^a ,
Mao Shuang ^a ,
Ren Yi ^b,*,,

a.
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068
b.
College of Chemistry, Sichuan University, Chengdu 610064

Corresponding author: Li Qianggen, liqgen@sina.com Ren Yi, renyi@scu.edu.cn
Received Date: 18 September 2016
Revised Date: 7 December 2016

Fund Project: the Research Funds of Sichuan Normal University 16ZP10Project supported by the National Natural Science Foundation of China 21202109the Research Fund of Department of Education, of Sichuan Province 13ZB0160

Figures(7)

Quantum chemical studies on the intramolecular N-arylation mechanism and reactivity of N-(2-halogen phenyl)-N'-phenyl ethyl amidines in dimethyl sulfoxide (DMSO) for the synthesis of benzimidazoles by base-catalyzed have been performed at MP2/6-311+G^**//B3LYP/6-311+G^** level of theory. The results indicate that the mechanism of the title reactions is not the radical mechanism or stepwise S_NAr pathway, but the concerted S_NAr pathway with a transition state, which is compared with the conclusion of Bolm et al. The reactivity of the title reactions can not be interpreted by the geometric looseness or natural population analysis. Multi parameter fitting reveals that the reactivity of the title reactions is controlled mostly by the regional nucleophilicity index ω_N10^- of the nucleophile N10 atom or highest occupied molecular orbital energy E_HOMO of the reactant, the other factor is the charges of the nucleophilic atom N10, while the charges of the C2 atom and the geometric looseness L% have almost no effect on the reaction energy barrier. The relative energies and the reactivity of the title reactions attained at MP2/6-311+G^**//B3LYP/6-311+G^** level of theory are better agreement with the experimental results compared with the other methods.
- intramolecular N-arylation,
- N-(2-halogen phenyl)-N'-phenyl ethyl amidines,
- reaction mechanism,
- S_NAr reaction,
- B3LYP,
- nucleophilicity index
1. [1]
  Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. doi: 10.1021/cr020033s
2. [2]
  Alamgir, M.; Black, D. St. C.; Kumar, N. Top. Heterocycl. Chem. 2007, 9, 87.
3. [3]
  Kedar, M. S.; Dighe, N. S.; Pattan, S. R.; Musmade, D. S.; Thakur, D.; Bhosale, M.; Gaware, V. M. Pharma Chem. 2010, 2, 249.
4. [4]
  Srikanth, L.; Varun Raj, V.; Raghunandan, N.; Venkateshwerlu, L. Pharma Chem. 2011, 3, 172.
5. [5]
  Narasimhan, B.; Sharma, D.; Kumar, P. Med. Chem. Res. 2012, 21, 269. doi: 10.1007/s00044-010-9533-9
6. [6]
  Lin, S. Y.; Isome, Y.; Stewart, E.; Liu, J. F.; Yohannes, D.; Yu, L. Tetrahedron Lett. 2006, 47, 2883. doi: 10.1016/j.tetlet.2006.02.127
7. [7]
  Dudd, L. M.; Venardou, E.; Garcia-Verdugo, E.; Licence, P.; Blake, A. J.; Wilson, C.; Poliakoff, M. Green Chem. 2003, 5, 187. doi: 10.1039/b212394k
8. [8]
  Zhang, C.; Zhang, L.; Jiao, N. Green Chem. 2012, 14, 3273. doi: 10.1039/c2gc36416f
9. [9]
  Chari, M. A.; Shobha, D.; Sasaki, T. Tetrahedron Lett. 2011, 52, 5575. doi: 10.1016/j.tetlet.2011.08.047
10. [10]
  Riadi, Y.; Mamouni, R.; Azzalou, R.; Haddad, M. E.; Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett. 2011, 52, 3492. doi: 10.1016/j.tetlet.2011.04.121
11. [11]
  Chari, M. A.; Shobha, D.; Kenawy, E. R.; Al-Deyab, S. S.; Reddy, B. V. S.; Vinu, A. Tetrahedron Lett. 2010, 51, 5195. doi: 10.1016/j.tetlet.2010.07.132
12. [12]
  Bahrami, K.; Khodaei, M. M.; Nejatia, A. Green Chem. 2010, 12, 1237. doi: 10.1039/c000047g
13. [13]
  Wan, J. P.; Gan, S. F.; Wu, J. M.; Pan, Y. Green Chem. 2009, 11, 1633. doi: 10.1039/b914286j
14. [14]
  Saha, D.; Saha, A.; Ranu, B. C. Green Chem. 2009, 11, 733. doi: 10.1039/b823543k
15. [15]
  Bahrami, K.; Khodaei, M. M.; Naali, F. Synlett 2009, 569.
16. [16]
  Sharghi, H.; Aberi, M.; Doroodmand, M. M. Adv. Synth. Catal. 2008, 350, 2380. doi: 10.1002/adsc.v350:14/15
17. [17]
  Mukhopadhyay, C.; Tapaswi, P. K. Tetrahedron Lett. 2008, 49, 6237. doi: 10.1016/j.tetlet.2008.08.041
18. [18]
  Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835. doi: 10.1021/jo8010232
19. [19]
  Zheng, N.; Anderson, K. W.; Huang, X.; Nguyen, H. N.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7509. doi: 10.1002/(ISSN)1521-3773
20. [20]
  Zheng, N.; Buchwald, S. L. Org. Lett. 2007, 9, 4749. doi: 10.1021/ol7020737
21. [21]
  Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598. doi: 10.1002/(ISSN)1521-3773
22. [22]
  Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 7974. doi: 10.1021/jo9017183
23. [23]
  Kim, Y.; Kumar, M. R.; Park, N.; Heo, Y., Lee, S. J. Org. Chem. 2011, 76, 9577. doi: 10.1021/jo2019416
24. [24]
  Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133. doi: 10.1021/ol027061h
25. [25]
  Brain, C. T.; Brunton, S. A. Tetrahedron Lett. 2002, 43, 1893. doi: 10.1016/S0040-4039(02)00132-6
26. [26]
  Brain, C. T.; Steer, J. T. J. Org. Chem. 2003, 68, 6814. doi: 10.1021/jo034824l
27. [27]
  Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. J. Org. Chem. 2011, 76, 716. doi: 10.1021/jo1021426
28. [28]
  Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932. doi: 10.1002/(ISSN)1521-3773
29. [29]
  Xiao, Q.; Wang, W.; Liu, G.; Meng, F.; Chen, J.; Yang, Z.; Shi, Z. Chem. Eur. J. 2009, 15, 7292. doi: 10.1002/chem.v15:30
30. [30]
  Wray, B. C.; Stambuli, J. P. Org. Lett. 2010, 12, 4576. doi: 10.1021/ol101899q
31. [31]
  Deng, X.; Mani, N. S. Eur. J. Org. Chem. 2010, 4, 680.
32. [32]
  Shen, M.; Driver, T. G. Org. Lett. 2008, 10, 3367. doi: 10.1021/ol801227f
33. [33]
  Cheng, Z.; Zhang, Q. F.; Xu, X. L.; Li, X. N. Chin. J. Org. Chem. 2015, 35(6), 1189 (in Chinese). doi: 10.6023/cjoc201411031
34. [34]
  Zhao, D. D.; Yu, J. T.; Wang, P. C.; Lu, M. Chin. J. Org. Chem. 2016, 36(1), 165 (in Chinese). ( doi: 10.6023/cjoc201507010
35. [35]
  Yu, Z. T.; Wang, Z. Y.; Wu, X.; Hu, G. Y.; Li, Q. B. Chin. J. Org. Chem. 2016, 36(7), 1672 (in Chinese). ( doi: 10.6023/cjoc201512007
36. [36]
  Meng, Y. X.; Gui, Y. Y.; Ji, Q.; Pan, Y.; L.; Lin, Z. Q.; Lü, L.; Zeng, X. C. Chin. J. Org. Chem. 2016, 36(2), 384 (in Chinese). doi: 10.6023/cjoc201507023
37. [37]
  Yuan, Y.; Thomé, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892. doi: 10.1002/adsc.v352.17
38. [38]
  Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654. doi: 10.1021/jo1022052
39. [39]
  Fang, Y.; Zheng, Y.; Wang, Z. Eur. J. Org. Chem. 2012, 7, 1495.
40. [40]
  Zou, L. H.; Reball, J.; Mottweiler, J.; Bolm, C. Chem. Commun. 2012, 48, 11307. doi: 10.1039/c2cc36711d
41. [41]
  Diness, F.; Fairlie, D. P. Angew. Chem., Int. Ed. 2012, 51, 8012. doi: 10.1002/anie.v51.32
42. [42]
  Carmen Pérez-Aguilar, M.; Valdés, C. Angew. Chem., Int. Ed. 2012, 51, 5953. doi: 10.1002/anie.201200683
43. [43]
  Jalalian, N.; Petersen, T. B.; Olofsson, B. Chem.-Eur. J. 2012, 18, 14140. doi: 10.1002/chem.v18.44
44. [44]
  Majumdar, K. C.; Ganai, S.; Nandi, R. K.; Ray, K. Tetrahedron Lett. 2012, 53, 1553. doi: 10.1016/j.tetlet.2012.01.015
45. [45]
  Zhao, J.; Zhao, Y.; Fu, H. Angew. Chem., Int. Ed. 2011, 50, 3769. doi: 10.1002/anie.v50.16
46. [46]
  Beyer, A.; Reucher, C. M. M.; Bolm, C. Org. Lett. 2011, 13, 2876. doi: 10.1021/ol2008878
47. [47]
  Thomé, I.; Bolm, C. Org. Lett. 2012, 14, 1892. doi: 10.1021/ol3005134
48. [48]
  Beyer, A.; Buendia, J.; Bolm, C. Org. Lett. 2012, 14, 3948. doi: 10.1021/ol301704z
49. [49]
  Thom, I.; Besson, C.; Kleine, T.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 7509. doi: 10.1002/anie.201300917
50. [50]
  Xiang, S. K.; Tan, W.; Zhang, D. X.; Tian, X. L.; Feng, C.; Wang, B. Q.; Zhao, K. Q.; Hu, P.; Yang, H. Org. Biomol. Chem. 2013, 11, 7271. doi: 10.1039/c3ob41479e
51. [51]
  Baars, H.; Beyer, A.; Kohlhepp, S. V.; Bolm, C. Org. Lett. 2014, 16, 536. doi: 10.1021/ol403414v
52. [52]
  Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273. doi: 10.1021/cr60153a002
53. [53]
  Terrier, F. The SNAr Reactions:Mechanistic Aspects, in Modern Nucleophilic Aromatic Substitution, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 2013, pp. 1~84.
54. [54]
  Hunter, A.; Renfrew, M.; Taylor, J. A.; Whitmore, J. M. J.; Wil-liams, A. J. Chem. Soc., Perkin Trans. 2 1993, 1703.
55. [55]
  Fernandez, I.; Frenking, G.; Uggerud, E. J. Org. Chem. 2010, 75(9), 2971. doi: 10.1021/jo100195w
56. [56]
  Glukhovtsev, M. N.; Bach, R. D.; Laiter, S. J. Org. Chem. 1997, 62(12), 4036. doi: 10.1021/jo962096e
57. [57]
  Simkin, B. Y.; Gluz, E. B.; Glukhovtsev, M. N.; Minkin, V. I. J. Mol. Struct. (THEOCHEM) 1993, 284(1~2), 123.
58. [58]
  Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
59. [59]
  Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
60. [60]
  Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200. doi: 10.1016/0009-2614(89)87234-3
61. [61]
  Jr, J. R. P.; Veloso, D. P. Phys. Chem. Chem. Phys. 2008, 10, 1118. doi: 10.1039/B716159J
62. [62]
  Cid, M. V. F.; Buijs, W.; Witkamp, G. J. Ind. Eng. Chem. Res. 2007, 46, 941.
63. [63]
  Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Sos. 2008, 130, 10848. doi: 10.1021/ja802533u
64. [64]
  Imoto, M.; Matsui, Y.; Takeda, M.; Tamaki, A.; Taniguchi, H.; Mizuno, K.; Ikeda, H. J. Org. Chem. 2011, 76, 6356. doi: 10.1021/jo2007219
65. [65]
  Toledo, R. O.; Santos, J. G.; Ríos, P.; Castro, E. A.; Campodónico, P. R.; Contreras, R. J. Phys. Chem. B 2013, 117, 5908. doi: 10.1021/jp4005295
66. [66]
  Toledo, R. O.; Contreras, R.; Tapiab, R. A.; Campodónico, P. R. Org. Biomol. Chem. 2013, 11, 2302. doi: 10.1039/c3ob27450k
67. [67]
  Du, L. J.; Wu, C. H.; Gu, H. H.; Li, J. J. Org. Chem. 2015, 35(8), 1726 (in Chinese).
68. [68]
  Glukhovtsev, M. N.; Bach, R. D.; Laiter, S. J. Org. Chem. 1997, 62, 4036. doi: 10.1021/jo962096e
69. [69]
  Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
70. [70]
  Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027. doi: 10.1021/cr00031a013
71. [71]
  Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899. doi: 10.1021/cr00088a005
72. [72]
  Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215. doi: 10.1007/s00214-007-0310-x
73. [73]
  Sadowsky, D.; McNeill, K.; Cramer, C. J. Environ. Sci. Technol. 2014, 48, 10904. doi: 10.1021/es5028822
74. [74]
  Cairns, A. G.; Senn, H. M.; Murphy, M. P.; Hartley, R. C. Chem. Eur. J. 2014, 20, 3742. doi: 10.1002/chem.v20.13
75. [75]
  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.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. J. A; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand. J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
76. [76]
  Glukhovtsev, M. N.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1996, 118, 6273. doi: 10.1021/ja953665n
77. [77]
  Li, Q. G.; Mao, S.; Cai, W. F.; Zheng, Y.; Liu, L. X. Chemistry 2016, 79(5), 418(in Chinese). (
78. [78]
  Shaik, S. S.; Schlegel, H. B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry. The S_N2 Mechanism, Wiley, New York, 1992, pp. 181~188.
79. [79]
  Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
80. [80]
  Chattaraj, P. K.; Sarkar, U.; Roy, D. R. Chem. Rev. 2006, 106, 2065. doi: 10.1021/cr040109f
81. [81]
  Ayers, P. W.; Anderson, J. S. M.; Bartolotti, L. J. Int. J. Quantum Chem. 2005, 101, 520. doi: 10.1002/(ISSN)1097-461X
82. [82]
  Contreras, R.; Andres, J.; Safont, V. S.; Campodonico, P.; Santos, J. G. J. Phys. Chem. A 2003, 107(29), 5588. doi: 10.1021/jp0302865
83. [83]
  Ormazábal-Toledo, R.; Contreras, R. Adv. Chem. 2014, 2014, 1.
84. [84]
  Ormazábal-Toledo, R.; Contreras, R.; Campodónico, P. R. J. Org. Chem. 2013, 78, 1091. doi: 10.1021/jo3025048
85. [85]
  Ormazábal-Toledo, R.; Campodónico, P. R.; Contreras, R. Org. Lett. 2011, 13, 822. doi: 10.1021/ol103033j
1. [1]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
2. [2]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
3. [3]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
4. [4]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
5. [5]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
6. [6]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
7. [7]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
8. [8]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
9. [9]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
10. [10]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
11. [11]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
12. [12]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
13. [13]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
14. [14]
  Lancanghong Chen , Xingtai Yu , Tianlei Zhao , Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089
15. [15]
  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
16. [16]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
17. [17]
  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
18. [18]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
19. [19]
  Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the A_E + A_N Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
20. [20]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(2001)
HTML views(805)

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