Citation: Chen-Fei SHEN, Zi-Zhong LIU, Hong-Xia LIU, Li-Nan HAN. Structures, Aromaticity and Raman Spectroscopy of Double Hanging Ring Molecules [(G_nH_n–1^m)(G_nH_n–1^m)] (G = C, Si, Ge; n = 3, 5, 6, 7, 8; m = +1, –1, 0, +1, +2)[J]. Chinese Journal of Structural Chemistry, ;2020, 39(2): 214-228. doi: 10.14102/j.cnki.0254–5861.2011–2416 shu

Structures, Aromaticity and Raman Spectroscopy of Double Hanging Ring Molecules [(G_nH_n–1^m)(G_nH_n–1^m)] (G = C, Si, Ge; n = 3, 5, 6, 7, 8; m = +1, –1, 0, +1, +2)

a.
Chemistry and Environment Science College, Inner Mongolia Normal University, Inner Mongolia Key Laboratory of Green Catalysis, Hohhot, Inner Mongolia 010022, China
b.
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China

Corresponding author: Zi-Zhong LIU, liuzz@imnu.edu.cn
Received Date: 18 April 2019
Accepted Date: 12 September 2019

Fund Project: the National Natural Science Foundation of China 21563023the Graduate Education Innovation Program funded Projects of Inner Mongolia S20161013506inner Mongolia Normal University Graduate Students' Research & Innovation Fund CXJJS16090

Figures(11)

Theoretical calculations of Double Hanging Ring Molecule (DHRM) [(G_nH_n–1^m)(G_nH_n–1^m)] (G = C, Si, Ge; n = 3, 5, 6, 7, 8; m = +1, –1, 0, +1, +2) were performed via Gaussian 09 with the method of Density Functional Theory (DFT). Geometrical optimization, Potential Energy surface Scan (PES), Degree of Aromaticity (DOA) and Nucleus Independent Chemical Shift (NICS) were computed to study the optimal structures and aromaticity of DHRMs. Ring Stretching Vibration Raman Spectroscopy (RSVRSF) was predicted to seek the relation between RSVRSF and aromaticity of DHRMs. The results show optimal structures of DHRMs[(G_nH_n–1^m)(G_nH_n–1^m)] (n = 3, 5~8); DA = 90° is the stable structure when n = 3, 7, 8; while n = 5 corresponds to DA = 30°, n = 6 corresponds to DA = 50°; the correlation between DOA and NICS of DHRMs is quadratic; the value of RSVRSF of DHRM approximates to its corresponding single ring molecule, which could act as characteristic frequency of ring molecule to identify its aromaticity; the correlation between RSVRSF and DOA is quadratic, and that between RSVRSF and NICS is linear.
1. [1]
  Kruszewski, J.; Krygowski, T. M. Definition of aromaticity basing on the harmonic oscillator model. Tetra. Lett. 1972, 13, 3839−3842. doi: 10.1016/S0040-4039(01)94175-9
2. [2]
  Mandal, D.; Maity, R.; Beg, H.; Salgado-M, G.; Misra, A. Computation of global reactivity descriptors and first hyper polarisability as a function of torsional angle of donor-acceptor substituted biphenyl ring system. Mol. Phys. 2017, 116, 1−11.
3. [3]
  Wei, X. Y.; Zhao, B. X.; Shang, Y. Z.; Cheng, Y. Z. Rigid biphenyl-contained epoxy resins with improved thermal resistant properties. Chin. J. Poly. Sci. 2017, 35, 1428−1435. doi: 10.1007/s10118-017-1975-9
4. [4]
  Boffetta, P.; Catalani, S.; Tomasi, C.; Pira, E.; Apostoli, P. Occupational exposure to polychlorinated biphenyls and risk of cutaneous melanoma. Eur. J. Cancer Prev. 2018, 27, 62−69. doi: 10.1097/CEJ.0000000000000316
5. [5]
  Tanabe, Y.; Mizuhata, Y.; Tokitoh, N. Synthesis and structure of a heavier congener of biphenyl, 1, 1΄-disila-4, 4΄-biphenyl. Organometallics 2010, 29, 721−723. doi: 10.1021/om901095w
6. [6]
  Guo, Y. B.; Liu, Z. Z.; Liu, H. X.; Zhang, F. Y.; Yin, J. Q. A new aromatic probe — the ring stretching vibration Raman spectroscopy frequency. Spectrochim. Acta A 2016, 164, 84−88. doi: 10.1016/j.saa.2016.03.005
7. [7]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT
8. [8]
  Shen, C. F.; Liu, Z. Z.; Liu, H. X.; Zhang, H. Q. Bond length equalization with molecular aromaticity-a new measurement of aromaticity. Spectrochim. Acta A 2018, 201.
9. [9]
  Cyranski, M. K. Energetic aspects of cyclic pi-electron delocalization, evaluation of the methods of estimating aromatic stabilization energies. Chem. Rev. 2005, 5, 3773−3811.
10. [10]
  Aihara, J. Effect of bond-length alternation on the aromaticity of benzene. Bull. Chem. Soc. Jpn. 1990, 63, 1956−1960. doi: 10.1246/bcsj.63.1956
11. [11]
  Aihara, J. Bond-length equalization and aromaticity in charged π-systems. Bull. Chem. Soc. Jpn. 2004, 77, 2179−2183. doi: 10.1246/bcsj.77.2179
12. [12]
  Solomon, P. M.; Norton, D. L. The biphenyl molecule as a model transistor. ACS Nano. 2008, 2, 435−440. doi: 10.1021/nn700253p
13. [13]
  Jiao, H.; Schleyer, P. V. R.; Mo, Y.; McAllister, M. A.; Tidwell, T. T. Magnetic evidence for the aromaticity and antiaromaticity of charged fluorenyl, indenyl, and cyclopentadienyl systems. J. Am. Chem. Soc. 1997, 119, 7075−7083. doi: 10.1021/ja970380x
14. [14]
  Mercero, J. M.; Ugalde, J. M. Sandwich-like complexes based on "all-metal" (Al 4 2-) aromatic compounds. J. Am. Chem. Soc. 2004, 126, 3380−3381. doi: 10.1021/ja039074b
15. [15]
  Liu, Z. Z.; Tian, W. Q.; Feng, J. K.; Zhang, G.; Li, W. Q. Theoretical study on structures and aromaticities of P5-anion, [Ti(η5-P5)]- and sandwich complex [Ti(η5-P5)2]₂. J. Phys. Chem. A 2005, 109, 5645−5655. doi: 10.1021/jp044395a
16. [16]
  Liu, Z. Z.; Tian, W. Q.; Feng, J. K.; Zhang, G.; Li, W. Q. The electronic structures and aromaticities for zinc sandwich, half-sandwich and zinc-zinc (Zn22+) sandwich complexes within density functional theory. J. Mol. Struc. Theochem. 2006, 758, 127−138. doi: 10.1016/j.theochem.2005.10.025
17. [17]
  Liu, Z. Z.; Tian, W. Q.; Feng, J. K.; Zhang, G.; Li, W. Q. A theoretical study on structures, bonding energies and aromaticity of two new series of dinuclear phosphametallocenes, (η5-P5) MM΄(η5-P5) and (η5-C₅H₅) MM΄(η5-P5) (M, M΄ = Zn, Cd). Eur. J. Inorg. Chem. 2006, 14, 2808−2818.
18. [18]
  Liu, Z. Z.; Tian, W. Q.; Feng, J. K.; Zhang, G.; Li, W. Q. Theoretical study on structures and aromaticities of a new series of sandwich complexes, [M2(η5P5)2] and [M(η5P5)2] (M = Be, Mg, and Ca). J. Mol. Struct. Theochem. 2007, 809, 171−179. doi: 10.1016/j.theochem.2007.01.020
19. [19]
  Schleyer, P. V. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; Hommes, N. J. R. V. E. Nucleus-independent chemical shifts, a simple and efficient aromaticity probe. J. Am. Chem. Soc. 1996, 118, 6317−6318. doi: 10.1021/ja960582d
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Structures, Aromaticity and Raman Spectroscopy of Double Hanging Ring Molecules [(GnHn–1m)(GnHn–1m)] (G = C, Si, Ge; n = 3, 5, 6, 7, 8; m = +1, –1, 0, +1, +2)

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通讯作者: 陈斌, bchen63@163.com

Structures, Aromaticity and Raman Spectroscopy of Double Hanging Ring Molecules [(G_nH_n–1^m)(G_nH_n–1^m)] (G = C, Si, Ge; n = 3, 5, 6, 7, 8; m = +1, –1, 0, +1, +2)