Citation: CHEN Xue-Song, LU Peng-Fei, DONG Yu-Hui, XIE Ju. Theoretical Study of Calix[4]pyrrole Complexes with Halide and AmmoniumIons[J]. Acta Physico-Chimica Sinica, ;2013, 29(10): 2187-2197. doi: 10.3866/PKU.WHXB201308142 shu

Theoretical Study of Calix[4]pyrrole Complexes with Halide and AmmoniumIons

1.
1 School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, Jiangsu Province, P. R. China;
2 Weifang University of Science and Technology, Weifang 262700, Shandong Province, P. R. China

Received Date: 21 May 2013
Available Online: 14 August 2013
Fund Project: 国家自然科学基金(21103147)资助项目 (21103147)

Density functional theory M06-2X/6-31G(d, p) was used on complexes of calix[4]pyrrole (CP) with halide anions (X^-=F^-, Cl^-, Br^-) and NH₄⁺-X^- ion-pairs. Geometries, binding energies, natural bond orbital analysis, and multifunctional wave function analysis (Multiwfn) were presented in detail. The results indicated that the interaction between the calix[4]pyrrole and halide anions mainly involved hydrogen (H)-bonds. Long-range van der Waals forces and steric effects were determined in the CP-Cl^- and CP-Br^- systems by Multiwfn analysis. Calix[4]pyrrole forms stable complexes with NH₄⁺-X^- ion-pairs mainly through H-bonds and electrostatic interactions, as well as via cation-π interactions. The 2:1 complexes of CP and anions or ion-pairs were also considered theoretically, but 2:1 is not the dominant stoichiometry relative to the 1:1 complexes. The current study also demonstrates that calix[4]pyrrole functions not only as an anion receptor, but also as a od ion-pair receptor, especially in cases involving fluoride ions.
- Calix[4]pyrrole,
- Anion and ion-pair,
- Host-guest interaction,
- Quantumchemistry calculation
1. [1]
  
  (1) Gale, P. A.; Anzenbacher, P.; Sessler, J. L. Coord. Chem. Rev.2001, 222, 57. doi: 10.1016/S0010-8545(01)00346-0
2. [2]
  (2) Allen, W. E.; Gale, P. A.; Brown, C. T.; Lynch, V. M.; Sessler, J.L. J. Am. Chem. Soc. 1996, 118, 12471. doi: 10.1021/ja9632217
3. [3]
  (3) Rambo, B. M.; Sessler, J. L. Chem. Eur. J. 2011, 17, 4946. doi: 10.1002/chem.v17.18
4. [4]
  (4) Cafeo, G.; Carbotti, G.; Cuzzola, A.; Fabbi, M.; Ferrini, S.;Kohnke, F. H.; Papanikolaou, G.; Plutino, M. R.; Rosano, C.;White, A. J. P. J. Am. Chem. Soc. 2013, 135, 2514 .
5. [5]
  (5) Blas, J. R.; Marquez, M.; Sessler, J. L.; Luque, F. J.; Orozco, M.J. Am. Chem. Soc. 2002, 124, 12796. doi: 10.1021/ja020318m
6. [6]
  (6) Wu, Y. D.; Wang, D. F.; Sessler, J. L. J. Org. Chem. 2001, 66,3739. doi: 10.1021/jo0016273
7. [7]
  (7) Pichierri, F. J. Mol. Struct. 2002, 581, 117.
8. [8]
  (8) Wintergerst, M. P.; Levitskaia, T. G.; Moyer, B. A.; Sessler, J.L.; Delmau, L. H. J. Am. Chem. Soc. 2008, 130, 4129.
9. [9]
  (9) Kriz, J.; Dybal, J.; Makrlik, E.; Sedlakova, Z. J. Chem. Phys.2012, 400, 19.
10. [10]
  (10) Xia, Y.; Wang, X.; Zhang, Y.; Luo, B.; Liu, Y. Journal of Molecular Modeling 2012, 18 (6), 2291.
11. [11]
  (11) Blas, J. R.; Marquez, M.; Sessler, J. L.; Luque, F. J.; Orozco, M.Chem. Eur. J. 2007, 13, 1108.
12. [12]
  (12) Zhao, Y.; Truhlar, D. G. Accounts Chem. Res. 2008, 41, 157.doi: 10.1021/ar700111a
13. [13]
  (13) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215. doi: 10.1007/s00214-007-0310-x
14. [14]
  (14) Sun, T.; Wang, Y. B. Acta Phys. -Chim. Sin. 2011, 27 (11), 2553.[孙涛, 王一波.物理化学学报, 2011, 27 (11), 2553.] doi: 10.3866/PKU.WHXB20111017
15. [15]
  (15) Weinhold, F.; Schleyer, P. v. R.; Clark, T.; Gasteiger, J.;Kollman, P. A.; SchaeferI, H. F., III; Schreiner, P. R.Encyclopedia of Computational Chemistry; John Wiley& Sons:Chichester, UK, 1998; Vol. 3, pp 1792-1811.
16. [16]
  (16) Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; et al . Gaussian 09,Revision B1; Gaussian Inc.: Wallingford, CT, 2010.
17. [17]
  (17) Johnson, E. R.; Keinan, S.; Mori-Sanchez, P.; Contreras-Garcia,J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498.
18. [18]
  (18) Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580.
19. [19]
  (19) Chen, P. Q.; Sun, H. W.; Chen, L.; Shen, R. X.; Yuan, M. X.;Lai, C. M. Chem. J. Chin. Univ. 2004, 25 (12), 2290. [陈沛全,孙宏伟,陈兰,沈荣欣, 袁满雪,赖城明.高等学校化学学报,2004, 25 (12), 2290.]
20. [20]
  (20) Liu, K.; Guo, Y.; Xu, J.; Shao, S. J.; Jiang, S. X. Chinese Chemical Letters 2006, 17 (3), 387.
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