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Structures of the phosphinidene germylenoid HP=GeLiF and its cycloaddition reaction with ethylene

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Abstract

The structures of phosphinidene germylenoid HP=GeLiF were studied for the first time by using DFT (density functional theory) calculations. The geometries were optimized at the B3LYP/6-311+G (d, p) level at first and then the single-point energies were calculated at QCISD/6-311++G (d, p) level. Theoretical calculations predicted that HP=GeLiF has two equilibrium structures, the p-complex (1) and the three-membered-ring (2) structures, in which structure 1 has the lower energy and is more stable than 2. To exploit the reactivity of HP=GeLiF, the cycloaddition reaction of 1 and ethylene was investigated at the same level of theory. From the potential energy profile, we predicted that the cycloaddition reaction has one dominant reaction pathway. The calculated result shows that the dominant reaction pathway is a [2 + 2] cycloaddition reaction which is the interaction of two π bonds in HP=GeLiF and ethylene molecule, and a four-membered-ring P-heterocyclic germylene is formed. Since sp3 hybridization of Ge atom in this four-membered-ring germylene, it may further react with another ethylene and finally forming a spiro-Ge-heterocyclic compound involving phosphorus. This means that this reaction involves a [2 + 2] cycloaddition as the initial step, and then a [2 + 1] cycloaddition carried out.

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References

  1. Harper WW, Ferrall EA, Hilliard RK, Stogner SM, Grev RS, Clouthier DJ (1997). J Am Chem Soc 119:8361–8362

    Article  CAS  Google Scholar 

  2. Boone AJ, Magers DH, Leszczyński J (1998). Int J Quantum Chem 70:925–932

    Article  CAS  Google Scholar 

  3. Stogner SM, Grev RS (1998). J Chem Phys 108:5458–5464

    Article  CAS  Google Scholar 

  4. Hostutler DA, Smith TC, Li H, Clouthier DJ (1999). J Chem Phys 111:950–958

    Article  CAS  Google Scholar 

  5. Liao HY, Su MD, Chu SY (2000). Inorg Chem 39:3522–3525

    Article  CAS  Google Scholar 

  6. Firme CL, Antunes OAC, Esteves PM (2009). Chem Phys Lett 468:129–133

    Article  CAS  Google Scholar 

  7. Lu XH, Han JF, Xu YH, Shi LY, Lian ZX (2010). Russ J Phys Chem A 84:980–986

    Article  CAS  Google Scholar 

  8. Hostutler DA, Clouthier DJ, Pauls SW (2002). J Chem Phys 116:1417–1423

    Article  CAS  Google Scholar 

  9. He SG, Tackett BS, Clouthier DJ (2004). J Chem Phys 121:257–264

    Article  CAS  Google Scholar 

  10. Lee VY, Sekiguchi A (2011). Inorg Chem 50:12303–12314

    Article  CAS  Google Scholar 

  11. Hao Q, Lu TX, Wilke JJ, Simmonett AC, Yamaguchi Y, Fang DC, Schaefer HF (2012). J Phys Chem A 116:4578–4589

    Article  CAS  Google Scholar 

  12. Lu XH, Lian ZX, Li YQ, Wang ZN (2012). Struct Chem 23:809–813

    Article  CAS  Google Scholar 

  13. Lu XH, Lian ZX, Li YQ, Wang ZN (2012). Struct Chem 23:1769–1775

    Article  CAS  Google Scholar 

  14. Lu XH, Lian ZX, Li YQ, Wang ZN (2012). J Mol Model 18(9):4209–4215

    Article  CAS  Google Scholar 

  15. Lu XH, Lian ZX, Li YQ, Wang ZN (2012). Russ J Phys Chem A 86:1869–1874

    Article  CAS  Google Scholar 

  16. Lu XH, Lian ZX, Liu DT, Bao WJ (2013). Int J Quantum Chem 113:1562–1567

    Article  CAS  Google Scholar 

  17. Lu XH, Li YQ, Bao WJ, Liu DT (2013). Comput Theor Chem 1007:76–81

    Article  CAS  Google Scholar 

  18. Lu XH, Li YQ, Liu DT, Bao WJ (2015). Res Chem Intermed 41:235–243

    Article  CAS  Google Scholar 

  19. Shoda S, Iwata S, Yajima K, Yagi K, Ohnishi Y, Kobayashi S (1997). Tetrahedron 53:15281–15295

    Article  CAS  Google Scholar 

  20. Iwamoto T, Masuda H, Ishida S, Kabuto C, Kira M (2004). J Organomet Chem 689:1337–1341

    Article  CAS  Google Scholar 

  21. Kassaee MZ, Ghambarian M, Musavi SM (2005). J Organomet Chem 690:4692–4703

    Article  CAS  Google Scholar 

  22. Filippou AC, Stumpf KW, Chernov O, Schnakenburg G (2012). Organometallics 31:748–755

    Article  CAS  Google Scholar 

  23. Li WZ, Yang FX, Cheng JB, Li QZ, Gong BA (2012). Chin J Struct Chem 31:19–26

    Google Scholar 

  24. Tan XJ, Wang WH, Li P, Wang QF, Zheng GX, Liu F (2008). J Organomet Chem 693:475–482

    Article  CAS  Google Scholar 

  25. Tan XJ, Wang WH, Li P, Liu F (2009). Russ J Phys Chem A 83:1355–1362

    Article  CAS  Google Scholar 

  26. Li WZ, Cheng JB, Gong BA, Xiao CP (2006). J Organomet Chem 691:5984–5987

    Article  CAS  Google Scholar 

  27. Li WZ, Tan HN, Xiao CP, Gong BA, Cheng JB (2007). Acta Phys -Chim Sin 23:1811–1814

    CAS  Google Scholar 

  28. Satge J, Couret C, Escudié J (1971). J Organomet Chem 30:c70–c74

    Article  CAS  Google Scholar 

  29. Couret C, Satge J, Andriamizaka JD, Escudie J (1978). J Organomet Chem 157:c35–c39

    Article  CAS  Google Scholar 

  30. Escudie J, Couret C, Andrianarison M, Satge J (1987). J Am Chem Soc 109:386–390

    Article  CAS  Google Scholar 

  31. Andrianarison M, Couret C, Declercq JP, Dubourg A, Escudie J, Ranaivonjatovo H, Satge J (1988). Organometallics 7:1545–1548

    Article  CAS  Google Scholar 

  32. Ranaivonjatovo H, Escudié J, Couret C, Satgé J (1991). J Organomet Chem 415:327–333

    Article  CAS  Google Scholar 

  33. Ranaivonjatovo H, Escudié J, Couret C, Declercq JP, Dubourg A, Satgé J (1993). Organometallics 12:1674–1681

    Article  CAS  Google Scholar 

  34. Kandrirodi A, Declercq JP, Dubourg A, Ranaivonjatovo H, Escudie J (1995). Organometallics 14:1954–1960

    Article  CAS  Google Scholar 

  35. Rodi AK, Ranaivonjatovo H, Escudié J, Kerbal A (1997). Phosphorus Sulfur 126:157–169

    Article  Google Scholar 

  36. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li H, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr PJE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A.01. Gaussian, Inc., Wallingford

    Google Scholar 

  37. Becke AD (1993). J Chem Phys 98:5648–5652

    Article  CAS  Google Scholar 

  38. Lee C, Yang W, Parr RG (1988). Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  39. Hehre WJ, Radom L, Schleyer PR, Pople JA (1986) Ab initio molecular orbital theory. Wiley, New York

    Google Scholar 

  40. Gauss J, Cremer D (1988). Chem Phys Lett 150:280–286

    Article  CAS  Google Scholar 

  41. Salter EA, Trucks GW, Bartlett RJ (1989). J Chem Phys 90:1752–1766

    Article  Google Scholar 

  42. Gonzalez C, Schlegel HB (1991). J Chem Phys 95:5853–5860

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation Committee of China (No. 21103145), the Natural Science Foundation of Shandong Province (No. ZR2016BM23), and the Special Foundation of Youth Academic Backbone of Yantai University.

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Authors and Affiliations

  1. The Laboratory of Theoretical and Computational Chemistry, College of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, People’s Republic of China

    Bingfei Yan, Tangmi Yuan, Wenzuo Li, Qingzhong Li & Jianbo Cheng

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  1. Bingfei Yan
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  2. Tangmi Yuan
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  3. Wenzuo Li
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  4. Qingzhong Li
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  5. Jianbo Cheng
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Correspondence to Bingfei Yan or Wenzuo Li.

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Yan, B., Yuan, T., Li, W. et al. Structures of the phosphinidene germylenoid HP=GeLiF and its cycloaddition reaction with ethylene. Struct Chem 29, 1647–1653 (2018). https://doi.org/10.1007/s11224-018-1142-0

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  • DOI: https://doi.org/10.1007/s11224-018-1142-0

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