Citation: Zhao Qing, Qi Boyu, Wang Baojin, Chen Feiwu. Theoretical Investigation on Weak Interactions of HXeBr with Benzene and Its Derivatives[J]. Acta Chimica Sinica, ;2015, 74(3): 285-292. doi: 10.6023/A15100641 shu

Theoretical Investigation on Weak Interactions of HXeBr with Benzene and Its Derivatives

1.
Department of Chemistry and Chemical Engineering, School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Beijing 100083

Corresponding author: Chen Feiwu, chenfeiwu@ustb.edu.cn
Received Date: 3 October 2015

Fund Project: the National Natural Science Foundation of China 21173020, 21473008

Figures(7)

Geometries of complexes HXeBr…C₆H₅X (X=H, CH₃, NH₂, N(CH₃)₂, NHCH₃, OH, OCH₃, CN, F, Cl, Br, I, COOH, SO₃H, CF₃) and its monomers are optimized with MP2/aug-cc-pVDZ (aug-cc-pVDZ-PP for Xe and I). The aug-cc-pVDZ-PP is a small core pseudopotential basis set. It ignores 28 electrons for Xe and I atoms. Two types of weak interactions, π…H bond and bifurcated hydrogen bonds, are analyzed in detail. The effects of substituting group of the benzene ring on the weak interaction energies are investigated. Their effects on π…H bond are different from that on bifurcated hydrogen bonds. As for the complexes with π…H bond, electron withdrawing groups reduce the interaction energies while electron donating groups increase the interaction energies. However, for the complexes with bifurcated hydrogen bonds, electron withdrawing groups increase the interaction energies while electron-donating groups decrease the interaction energies. The effects of substituting groups on geometrical parameters of HXeBr are also analyzed. As for 14 complexes of HXeBr…C₆H₅X with bifurcated hydrogen bonds, it is found that their weak interaction energies have very good linear relationships with dipole moments of C₆H₅X, bond length changes of Xe—Br and H—Xe bonds, vibrational frequency changes of H—Xe bonds, and the sum of two interpenetration distances of Van der Waals surfaces of bromine and two hydrogen atoms which are connected to the bromine atom by hydrogen bonds. It is also found that the weak interaction energies of 14 complexes above have very good linear relationships with the sum of electron densities (ρ), the sum of ∇²ρ and the sum of electrostatic potentials at two critical points of bifurcated hydrogen bonds, and with the electron density, ∇²ρ and the electrostatic potential at the ring critical point which is inside a ring formed by the bifurcated hydrogen bonds and two carbon atoms of the benzene ring. As for the complexes with bifurcated hydrogen bonds, the weak interaction energies between the monomers can be understood approximately as dipole-dipole interaction.
- rare gas,
- HXeBr,
- benzene,
- π…H bond,
- bifurcated hydrogen bonds
1. [1]
  Klemperer, W. Science 1992, 257, 887.
2. [2]
  Rozas, I.; Alkorta, I.; Elguero, J. J. Phys. Chem. A 1997, 101, 4236.
3. [3]
  Rozas, I.; Alkorta, I.; Elguero, J. J. Phys. Chem. A 1998, 102, 9925.
4. [4]
  Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253.
5. [5]
  Tarakeshwar, P.; Choi, H. S.; Kim, K. S. J. Am. Chem. Soc. 2001, 123, 3323.
6. [6]
  Grabowski, S. J.; Sokalski, W. A.; Leszczynski, J. J. Phys. Chem. A 2004, 108, 5823.
7. [7]
8. [8]
9. [9]
10. [10]
  Bartlett, N. Proc. Chem. Soc. 1962, 218.
11. [11]
  Pettersson, M.; Lundell, J.; Räsänen, M. J. Chem. Phys. 1995, 102, 6423.
12. [12]
  Khriachtchev, L.; Pettersson, M.; Runeberg, N.; Lundell, J.; Räsänen, M. Nature 2000, 406, 874.
13. [13]
  Lignell, A.; Khriachtchev, L.; Pettersson, M.; Räsänen, M. J. Chem. Phys. 2003, 118, 11120.
14. [14]
  McDowell, S. A. C. J. Chem. Phys. 2004, 120, 3630.
15. [15]
  McDowell, S. A. C. Chem. Phys. Lett. 2005, 406, 228.
16. [16]
  Yen, S.-Y.; Mou, C.-H.; Hu, W.-P. Chem. Phys. Lett. 2004, 383, 606.
17. [17]
  Liu, X.-F.; Li, Q.-Z.; Li, R.; Li, W.-Z.; Cheng, J.-B. Spectrochim. Acta A 2011, 84, 68.
18. [18]
  Lignell, A.; Lundell, J.; Khriachtchev, L.; Räsänen, M. J. Phys. Chem. A 2008, 112, 5486.
19. [19]
  Tsuge, M.; Berski, S.; Stachowski, R.; Räsänen, M.; Latajka, Z.; Khriachtchev, L.J. Phys. Chem. A 2012, 116, 4510.
20. [20]
  Tsivion, E.; Räsänen, M.; Gerber, R. B. Phys. Chem. Chem. Phys. 2013, 15, 12610.
21. [21]
  Tsuge, M.; Berski, S.; Räsänen, M.; Latajka, Z.; Khriachtchev, L.J. Chem. Phys. 2014, 140, 044323.
22. [22]
  Peterson, K. A.; Figgen, D.; Goll, E.; Stoll, H.; Dolg, M. J. Chem. Phys. 2003, 119, 11113.
23. [23]
  Feller, D. J. Comp. Chem. 1996, 17, 1571.(b) Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47, 1045.
24. [24]
  Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
25. [25]
  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. A.; Jr., Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.;Keith, T.; 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, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01, Gaussian,Inc., Wallingford CT, 2009.
26. [26]
  Lu, T.; Chen, F.-W. J. Comput. Chem. 2012, 33, 580.(b) Multiwfn website:http://Multiwfn.codeplex.com.
27. [27]
  Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics Modell. 1996, 14, 33.
28. [28]
  Bader, R. F. W. Chem. Rev. 1991, 91, 893.
29. [29]
  Bader, R. W. F. Acc. Chem. Res. 1985, 18, 9.
30. [30]
  Bader, R. F. W. Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, 1990.
31. [31]
  Lu, T.; Chen, F.-W. J. Theor. Comput. Chem. 2012, 11, 163.
32. [32]
  Ammal, S. S. C.; Venuvanalingam, P. J. Chem. Phys. 1998, 109, 9820.
33. [33]
34. [34]
  Grimme, S. Angew. Chem., Int. Ed. 2008, 47, 3430.
35. [35]
  Joseph, J.; Jemmis, E. D. J. Am. Chem. Soc. 2007, 129, 4620.
1. [1]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
2. [2]
  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
3. [3]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
4. [4]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
5. [5]
  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
6. [6]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
7. [7]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
8. [8]
  Kun Zou , Yihang Xiao , Jinyu Yang , Mingxuan Wu . Facile semisynthesis of histone H3 enables nucleosome probes for investigation of histone H3K79 modifications. Chinese Chemical Letters, 2024, 35(10): 109497-. doi: 10.1016/j.cclet.2024.109497
9. [9]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
10. [10]
  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
11. [11]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
12. [12]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
13. [13]
  Jia-Mei Qin , Xue Li , Wei Lang , Fu-Hao Zhang , Qian-Yong Cao . An AIEgen nano-assembly for simultaneous detection of ATP and H₂S. Chinese Chemical Letters, 2024, 35(6): 108925-. doi: 10.1016/j.cclet.2023.108925
14. [14]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
15. [15]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
16. [16]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
17. [17]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
18. [18]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
19. [19]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
20. [20]
  Yuanchao LI , Weifeng HUANG , Pengchao LIANG , Zifang ZHAO , Baoyan XING , Dongliang YAN , Li YANG , Songlin WANG . Effect of heterogeneous dual carbon sources on electrochemical properties of LiMn_0.8Fe_0.2PO₄/C composites. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 751-760. doi: 10.11862/CJIC.20230252

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(989)
HTML views(198)

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