H3XF (X = Ge, Si)与芳香环化合物间硅键作用的理论研究
Theoretical Study of Tetrel-Bonding Interactions between H3XF (X = Ge, Si) and Aromatic Ring Compounds
DOI: 10.12677/JAPC.2019.82006, PDF,    国家科技经费支持
作者: 颜锐朋, 朱冉靖, 苏奕帆, 李俊玲, 陈益山*：曲靖师范学院，化学与环境科学学院，云南 曲靖
关键词: 硅键；σ-Hole；MP2；静电势；相互作用能；Tetrel Bonding； σ-Hole； MP2； Electrostatic Potential； Interaction Energy
摘要: 通过量子化学计算方法MP2对H3XF (X = Ge, Si)和五种芳香环化合物(苯、吡啶、吡咯、呋喃、噻吩)形成的硅键复合物进行了研究。复合物的结合模式可分为两类，模式I复合物中X主要与芳香环碳原子发生硅键相互作用，模式II则主要与芳香环杂原子发生硅键相互作用。H3XF与所有芳香环化合物都能形成模式I复合物，稳定性顺序为：吡咯 > 噻吩 > 苯 > 呋喃 > 吡啶。H3XF则只能与三种芳香环化合物形成模式II复合物，稳定性顺序为：吡啶 > 噻吩 > 呋喃。分析表明模式I复合物均为π型硅键，而模式II复合物则各不同：吡啶模式II复合物为n型硅键，呋喃模式II复合物为n/π型硅键，噻吩模式II复合物为π型硅键。
Abstract: The tetrel-bonding complexes formed between H3XF (X = Ge, Si) and the selected aromatic ring compounds (benzene, pyridine, pyrrole, furan and thiophene) have been investigated by MP2 quantum chemical method. There exist two binding modes for these complexes. The X atoms mainly interact with the carbon atoms of aromatic ring compounds for mode I complexes, while the X atoms mainly interact with the hetero atoms for binding mode II complexes. All the aromatic ring compounds can form mode I complexes with H3XF, and the order of stability is pyrrole > thiophene > benzene > furan > pyridine. Only three aromatic ring compounds can form mode II complexes with H3XF, and the order of stability is pyridine > thiophene > furan. All the five mode I complexes are π-type tetrel-bonding complexes, but the mode II complexes are different from each other: the mode II complex of pyridine is n-type complex; the mode II complex of furan is n/π-type complex; and the mode II complex of thiophene is π-type complex.
文章引用：颜锐朋, 朱冉靖, 苏奕帆, 李俊玲, 陈益山. H3XF (X = Ge, Si)与芳香环化合物间硅键作用的理论研究[J]. 物理化学进展, 2019, 8(2): 47-58. https://doi.org/10.12677/JAPC.2019.82006

参考文献

[1] Politzer, P., Murray, J.S. and Clark, T. (2013) Halogen Bonding and Other σ-Hole Interactions: A Perspective. Physical Chemistry Chemical Physics, 15, 11178-11189. [Google Scholar] [CrossRef] [PubMed]
[2] Frontera, A., Quiñonero, D. and Deyà, P.M. (2011) Cation-π and Anion-π Interactions. Molecular Sciences, 1, 440-459. [Google Scholar] [CrossRef] 
[3] Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. and Terraneo, G. (2008) Halogen Bonding in Supramolecular Chemistry. Angewandte Chemie In-ternational Edition, 47, 6114-6127. [Google Scholar] [CrossRef] [PubMed]
[4] Hernandes, M.Z., Cavalcanti, S.M.T., Moreira, D.R.M., de Azevedo Jr., W.F. and Leite, A.C.L. (2010) Halogen Atoms in the Modern Medicinal Chemistry: Hints for the Drug De-sign. Current Drug Targets, 11, 303-314. [Google Scholar] [CrossRef] [PubMed]
[5] Wang, W., Ji, B. and Zhang, Y. (2009) Chalcogen Bond: A Sister Noncovalent Bond to Halogen Bond. The Journal of Physical Chemistry A, 113, 8132-8135. [Google Scholar] [CrossRef] [PubMed]
[6] Zahn, S., Frank, R., Hey-Hawkins, E. and Kirchner, B. (2011) Barbara Kirchner. Chemistry—A European Journal, 17, 6034-6038. [Google Scholar] [CrossRef] [PubMed]
[7] Li, Q.Z., Li, R., Liu, X.F., Li, W.Z. and Cheng, J.B. (2012) Concerted Interaction between Pnicogen and Halogen Bonds in XCl-FH2P-NH3 (X = F, OH, CN, NC, and FCC). ChemPhysChem, 13, 1205-1212. [Google Scholar] [CrossRef] [PubMed]
[8] Li, Q.Z., Li, R., Liu, X.F., Li, W.Z. and Cheng, J.B.J. (2012) Pnicogen-Hydride Interaction between FH2X (X = P and As) and HM (M = ZnH, BeH, MgH, Li, and Na). The Journal of Physical Chemistry A, 116, 2547-2553. [Google Scholar] [CrossRef] [PubMed]
[9] 刘玉震, 黎安勇. H2XP•••SHY复合物中磷键与硫键的理论研究[J]. 物理化学学报, 2015, 31(3): 435-440.
[10] Bauza, A., Mooibroek, T.J. and Frontera, A. (2013) Tetrel-Bonding Interaction: Rediscovered Supramolecular Force? Angewandte Chemie International Edition, 52, 12317-12321. [Google Scholar] [CrossRef] [PubMed]
[11] Dong, W.B., Niu, B.B., Liu, S.F., Cheng, J.B., Liu, S.L. and Li, Q.Z. (2019) Comparison of σ-/π-Hole Tetrel Bonds between TH3F/F2TO and H2CX (X = O, S, Se). ChemPhysChem, 20, 627-635.
[12] Wei, Y.X., Li, Q.Z. and Steve, S. (2018) The π-Tetrel Bond and Its Influence on Hydrogen Bonding and Proton Transfer. ChemPhysChem, 19, 736-743. [Google Scholar] [CrossRef] [PubMed]
[13] Mo, L.X., Zeng, Y.L., Li, X.Y. and Meng, L.P. (2017) The Enhancing Effects of Molecule X (X  =  PH2Cl, SHCl, ClCl) on Chalcogen-Chalcogen Interactions in Cyclic Trimers Y•••Y•••X (Y  =  SHCl, SeHCl). International Journal of Quantum Chemistry, 117, e25354. [Google Scholar] [CrossRef] 
[14] Mehdi, D., Esrafili, S.A. and Parisasadat, M. (2018) Anionic Tetrel Bonds: An Ab Initio Study. Chemical Physics Letters, 691, 394-400. [Google Scholar] [CrossRef] 
[15] Xu, H.L., Cheng, J.B., Yang, X., Liu, Z.B., Li, W.Z. and Li, Q.Z. (2017) Comparison of σ-Hole and π-Hole Tetrel Bonds Formed by Pyrazine and 1,4-Dicyanobenzene: The Interplay between Anion-π and Tetrel Bonds. ChemPhysChem, 18, 2442-2450. [Google Scholar] [CrossRef] [PubMed]
[16] Wu, J.Y. (2014) Investigations into the Nature of Halogen- and Hydrogen-Bonding Interactions of Some Heteroaromatic Rings with Dichlorine Monoxide. Journal of Molecular Modeling, 20, 2424. [Google Scholar] [CrossRef] [PubMed]
[17] 许惠英, 王维, 邹建卫. PH2X与五元杂环体系磷键相互作用的理论研究[J]. 化学学报, 2013, 71(8): 1175-1182.
[18] Boys, S.F. (1970) The Calculation of Small Molecular Interactions by the Differences of Separate Total Energies. Some Procedures with Reduced Errors. Molecular Physics, 19, 553-566. [Google Scholar] [CrossRef] 
[19] Reed, A.E., Weinhold, F., Curtiss, L.A. and Pochatko, D.J. (1988) Intermo-lecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint. Chemical Reviews, 88, 899-926. [Google Scholar] [CrossRef] 
[20] Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al. (2009) Gaussian 09. Revision C.01. Gaussian Inc., Wallingford.
[21] Dennington, R., Keith, T. and Millam, J.S. (2009) GaussView, Version 5. Semichem Inc., Shawnee Mission.
[22] Grabowski, S.J. (2001) Ab Initio Calculations on Conventional and Unconventional Hydrogen Bonds Study of the Hydrogen Bond Strength. The Journal of Physical Chemistry A, 105, 10739-10746. [Google Scholar] [CrossRef] 
[23] Scheiner, S., Grabowski, S.J. and Kar, T.J. (2001) Influence of Hybridization and Sub-stitution on the Properties of the CH•••O Hydrogen Bond. The Journal of Physical Chemistry A, 105, 10607-10612. [Google Scholar] [CrossRef] 
[24] Johnson, E.R., Keinan, S., Mori-Sánchez, P., Contreras-García, J., Cohen, A.J. and Yang, W.T. (2010) Revealing Noncovalent Interactions. Journal of the American Chemical Society, 132, 6498-6506. [Google Scholar] [CrossRef] [PubMed]
[25] Lu, T. and Chen, F.W. (2012) A Multifunctional Wavefunction Analyzer. Journal of Computational Chemistry, 33, 580-592. [Google Scholar] [CrossRef] [PubMed]
[26] Humphrey, W., Dalke, A. and Schulten, K. (1996) VMD—Visual Molecular Dynamics. Journal of Molecular Graphics, 14, 33-38. [Google Scholar] [CrossRef] [PubMed]