Citation: TAO Sha, YU Li-Juan, WU De-Yin, TIAN Zhong-Qun. Raman Spectra of Amino Wagging Vibrational Modes in p-π-Conjugated Molecules[J]. Acta Physico-Chimica Sinica, ;2013, 29(08): 1609-1617. doi: 10.3866/PKU.WHXB201306032 shu

Raman Spectra of Amino Wagging Vibrational Modes in p-π-Conjugated Molecules

1.
State Key Laboratory for Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China

Received Date: 16 April 2013
Available Online: 3 June 2013
Fund Project: 国家自然科学基金(91027009, 21021002, 20973143) (91027009, 21021002, 20973143) 国家重点基础研究发展规划项目(973) (2009CB930703) (973) (2009CB930703)厦门大学(2010121020)资助 (2010121020)

Raman spectroscopy has been widely used as a non-destructive testing and molecular recognition technology, providing fingerprint information for chemical and biological molecular structures. One type of out-of-plane bending vibration observed in Raman spectroscopy is named the‘wagging vibration’. The Raman signal of the wagging mode is very sensitive; not only the vibrational frequency but also the Raman intensity depends strongly on environment factors. In this report, density functional theory (DFT) calculations are used to study the equilibrium structures, binding interactions, and Raman spectra of vinylamine and aniline as well as their complexes with silver clusters and water clusters. Vinylamine-silver and aniline-silver clusters were used to simulate the interactions of the molecules adsorbed on silver surfaces, while vinylamine-water and aniline-water clusters were used to investigate the hydrogen bonding interactions of vinylamine and aniline with water clusters. Our calculated results show that the Raman signal of the amino wagging mode strongly depends on the hydrogen bonding interaction of the nitrogen lone pair in the amino group with the O―H bond of water. Increasing the size of the water clusters causes a large blue shift and considerable enhancement in the intensity of the wagging vibration. When the polarized continuum model was used to consider the solvation effect, the electrostatic interaction contributing to the hydrogen bond was weakened. In this case, the simulated Raman spectra were similar to each other. For vinylamine and aniline interacting with silver clusters, the Raman signals of the amino wagging vibration were changed by the weak binding interaction, revealing the relationship between the abnormal signal of wagging vibrations and the weak interaction in p-π-conjugated systems.
- Wagging vibration mode,
- Weak intermolecular interaction,
- Hydrogen bond,
- Vinylamine,
- Aniline,
- Raman spectroscopy,
- Density functional theory
1. [1]
  
  (1) Krueger, P. Canadian Journal of Chemistry 1963, 41, 363. doi: 10.1139/v63-053
2. [2]
  (2) Xie, M., X.; Liu, Y. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2002, 58, 2817. doi: 10.1016/S1386-1425(02)00072-0
3. [3]
  (3) Solca, N.; Dopfer, O. The European Physical Journal D-Atomic, Molecular, Optical and Plasma Physics 2002, 20, 469.
4. [4]
  (4) Szatylowicz, H.; Kry wski, T. M.; Hobza, P. The Journal of Physical Chemistry A 2007, 111, 170. doi: 10.1021/jp065336v
5. [5]
  (5) Wolff, H.; Mathias, D. The Journal of Physical Chemistry 1973,77, 2081. doi: 10.1021/j100636a010
6. [6]
  (6) Nakanaga, T.; Ito, F.; Miyawaki, J.; Sugawara, K.; Takeo, H.Chemical Physics Letters 1996, 261, 414. doi: 10.1016/0009-2614(96)00994-3
7. [7]
  (7) Nakanaga, T.; Kawamata, K.; Ito, F. Chemical Physics Letters1997, 279, 309. doi: 10.1016/S0009-2614(97)01059-2
8. [8]
  (8) Nakanaga, T.; Sugawara, K.; Kawamata, K.; Ito, F. Chemical Physics Letters 1997, 267, 491. doi: 10.1016/S0009-2614(97)00127-9
9. [9]
  (9) Schmid, R.; Chowdhury, P.; Miyawaki, J.; Ito, F.; Sugawara, K.;Nakanaga, T.; Takeo, H.; Jones, H. Chemical Physics 1997, 218,291. doi: 10.1016/S0301-0104(97)00072-4
10. [10]
  (10) Fedotova, M. V.; Kruchinin, S. E. Journal of Molecular Liquids2013, 179, 27. doi: 10.1016/j.molliq.2012.11.031
11. [11]
  (11) Plugatyr, A.; Svishchev, I. M. The Journal of Chemical Physics2009, 130, 114509. doi: 10.1063/1.3096672
12. [12]
  (12) Li, D.W.; Qu, L. L.; Zhai,W. L.; Xue, J. Q.; Fossey, J. S.; Long,Y. T. Environmental Science & Technology 2011, 45, 4046. doi: 10.1021/es104155r
13. [13]
  (13) Perry, D. A.; Cordova, J. S.; Schiefer, E. M.; Chen, T. Y.; Razer,T. M.; Biris, A. S. The Journal of Physical Chemistry C 2012,116, 4584. doi: 10.1021/jp208489w
14. [14]
  (14) Wu, D. Y.; Liu, X. M.; Huang, Y. F.; Ren, B.; Xu, X.; Tian, Z. Q.The Journal of Physical Chemistry C 2009, 113, 18212. doi: 10.1021/jp9050929
15. [15]
  (15) Tian, Z. Q.; Lei, L. C.; Jing, X. B. Acta Phys. -Chim. Sin. 1988,4, 458. [田中群, 雷良才, 景遐斌. 物理化学学报, 1988, 4,458.] doi: 10.3866/PKU.WHXB19880504
16. [16]
  (16) Park, H.; Lee, S. B.; Kim, K.; Kim, M. S. The Journal of Physical Chemistry 1990, 94, 7576.
17. [17]
  (17) Park, S. H.; Kim, K.; Kim, M. S. Journal of Molecular Structure1993, 301, 57. doi: 10.1016/0022-2860(93)80231-J
18. [18]
  (18) Zhao, L. B.; Huang, R.; Bai, M. X.;Wu, D. Y.; Tian, Z. Q. The Journal of Physical Chemistry C 2011, 115, 4174. doi: 10.1021/jp1117135
19. [19]
  (19) Hamada, Y.; Sato, N.; Tsuboi, M. Journal of Molecular Spectroscopy 1987, 124, 172. doi: 10.1016/0022-2852(87)90130-5
20. [20]
  (20) McNaughton, D.; Evans, C. J. Journal of Molecular Spectroscopy 1999, 196, 274. doi: 10.1006/jmsp.1999.7861
21. [21]
  (21) Brown, R.; dfrey, P.; Kleibomer, B.; Pierlot, A.;McNaughton, D. Journal of Molecular Spectroscopy 1990, 142,195. doi: 10.1016/0022-2852(90)90177-R
22. [22]
  (22) Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. The Journal of Physical Chemistry B 2009, 113, 6378. doi: 10.1021/jp810292n
23. [23]
  (23) Wu, D. Y.; Hayashi, M.; Shiu, Y. J.; Liang, K. K.; Chang, C. H.;Yeh, Y. L.; Lin, S. H. The Journal of Physical Chemistry A2003, 107, 9658. doi: 10.1021/jp034951l
24. [24]
  (24) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09,Revision A. 01; Gaussian Inc.:Wallingford, CT, 2009.
25. [25]
  (25) McLean, A.; Chandler, G. The Journal of Chemical Physics1980, 72, 5639. doi: 10.1063/1.438980
26. [26]
  (26) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. The Journal of Chemical Physics 1980, 72, 650. doi: 10.1063/1.438955
27. [27]
  (27) Wadt,W. R.; Hay, P. J. The Journal of Chemical Physics 1985,82, 284. doi: 10.1063/1.448800
28. [28]
  (28) Hay, P. J.;Wadt,W. R. The Journal of Chemical Physics 1985,82, 299. doi: 10.1063/1.448975
29. [29]
  (29) Schultz, G.; Portalone, G.; Ramondo, F.; Domenicano, A.;Hargittai, I. Structural Chemistry 1996, 7, 59. doi: 10.1007/BF02275450
30. [30]
  (30) Boys, S.; Bernardi, F. Molecular Physics 1970, 19, 553. doi: 10.1080/00268977000101561
31. [31]
  (31) Reed, A. E.; Curtiss, L. A.;Weinhold, F. Chemical Reviews1988, 88, 899. doi: 10.1021/cr00088a005
32. [32]
  (32) Carpenter, J.;Weinhold, F. Journal of Molecular Structure: Theochem 1988, 169, 41. doi: 10.1016/0166-1280(88)80248-3
33. [33]
  (33) Liang, X. J.; Cui, L.;Wu, D. Y.; Tian, Z. Q. Acta Phys. -Chim. Sin. 2009, 25, 1605 [梁晓静, 崔丽, 吴德印, 田中群. 物理化学学报, 2009, 25, 1605.] doi: 10.3866/PKU.WHXB20090808
34. [34]
  (34) Ziegler, L.; Hudson, B. The Journal of Physical Chemistry1984, 88, 1110. doi: 10.1021/j150650a016
35. [35]
  (35) Tsuboi, M.; Hirakawa, A. Y.; Ino, T.; Sasaki, T.; Tamagake, K.The Journal of Chemical Physics 1964, 41, 2721. doi: 10.1063/1.1726344
36. [36]
  (36) Evans, J. Spectrochimica Acta 1960, 16, 428. doi: 10.1016/0371-1951(60)80037-9
37. [37]
  (37) Larsen, N.; Hansen, E.; Nicolaisen, F. Chemical Physics Letters1976, 43, 584. doi: 10.1016/0009-2614(76)80629-X
38. [38]
  (38) Rauhut, G.; Pulay, P. The Journal of Physical Chemistry 1995,99, 3093. doi: 10.1021/j100010a019
39. [39]
  (39) Shindo, H. J. Chem. Soc. Faraday Trans. 1 1986, 82, 45. doi: 10.1039/f19868200045
40. [40]
  (40) Holze, R. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry 1988, 250, 143. doi: 10.1016/0022-0728(88)80199-2
41. [41]
  (41) Tripathi, G. The Journal of Chemical Physics 1980, 73, 5521.doi: 10.1063/1.440072
42. [42]
  (42) Qi, Y.; Hu, Y.; Xie, M.; Xing, D.; Gu, H. Journal of Raman Spectroscopy 2011, 42, 1287. doi: 10.1002/jrs.v42.6
43. [43]
  (43) Funnell, N. P.; Dawson, A.; Marshall,W. G.; Parsons, S.CrystEngComm 2013, 15, 1047.
44. [44]
  (44) Wojciechowski, P. M.; Zierkiewicz,W.; Michalska, D.; Hobza,P. The Journal of Chemical Physics 2003, 118, 10900. doi: 10.1063/1.1574788
45. [45]
  (45) Chrétien, S.; rdon, M. S.; Metiu, H. The Journal of Chemical Physics 2004, 121, 9925. doi: 10.1063/1.1809600
46. [46]
  (46) Soto-Verdu , V.; Metiu, H.; Gwinn, E. The Journal of Chemical Physics 2010, 132, 195102. doi: 10.1063/1.3419930
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