Citation: JIN Qin, SUN Xiao-Ling, WANG Yan-Ni, WEI Tao, WANG Chao-Jie. Computational Study on the Coordinate Systems of Proline with Cu, Cu⁺ and Cu²⁺[J]. Acta Physico-Chimica Sinica, ;2014, 30(7): 1247-1258. doi: 10.3866/PKU.WHXB201405141 shu

Computational Study on the Coordinate Systems of Proline with Cu, Cu⁺ and Cu²⁺

1.
Pharmacy School of Wenzhou Medical University, Wenzhou 325035, Zhejiang Province, P. R. China

Received Date: 28 February 2014
Available Online: 14 May 2014
Fund Project:

The geometric and electronic structures, energetics, and vibrational frequencies of different coordinate systems formed between 15 conformers of proline (Pro) and Cu, Cu⁺, and Cu²⁺ were investigated in detail, using the M06-2X and ωB97XDmethods with 6-311++G(2d, p) and TZVPbasis sets.Atotal of 20, 16, and 16 stable [Pro-Cu]^0/1+/2+ complexes were obtained at four levels. These structures demonstrated that 12 conformers of Pro exist in the [Pro-Cu] and [Pro-Cu]⁺ systems, while 11 conformers are present in the [Pro-Cu]²⁺ complexes. The most stable complexes are evidently not formed by the lowest energy conformer of Pro with Cu, Cu⁺, and Cu²⁺. In the CI3, CI4, CII7, and CII8 complexes, the carboxyl group hydrogen of Pro was found to transfer to the imino nitrogen to forma zwitterion. Both the relative energy difference and the deformation energy of Pro gradually increase along with the charge number of the Cu. The binding energies of the [Pro-Cu]^0/1+/2+ systems were determined to be in the ranges of -60.0 to -5.0, -340.0 to -170.0, and -1100.0 to -860.0 kJ· mol^-1, respectively. The stretching vibrational frequencies of the N―H and O―H bonds in Pro all exhibit a general red shift on complexation. Additionally, each systemshows charge transfer fromthe Pro to the Cu, even in the case of [Pro-Cu]²⁺, some complexes that have more than one negative charge.
- M06-2X,
- ωB97XD,
- Proline,
- Copper atom,
- Copper ion
1. [1]
  
  (1) Xiao, H. R.; Shi, C. H.; Xia, B. L.; Sheng, L. Q.; Zhang, Y. G.; Liu, Q. L. Chin. J. Inorg. Chem. 2003, 19, 589. [肖厚荣, 施春华,夏炳乐, 盛良全,张艳鸽, 刘清亮.无机化学学报, 2003, 19, 589.]
2. [2]
  (2) Wang, J. Y.; Zheng, X. F.; An, L. J.; Gai, H. W.; Hu, J. H. Spectroscopy and Spectral Analysis 2001, 21, 432. [王静云, 郑学仿, 安利佳, 盖宏伟,胡皆汉. 光谱学与光谱分析, 2001, 21, 432.]
3. [3]
  (3) Zheng, X. F.; Wang, J. Y.; Wang, Y.; An, L. J.; Gai, H. W.; Hu, J. H. Spectroscopy and Spectral Analysis 2001, 21, 804. [郑学仿, 王静云, 王园, 安利佳,盖宏伟, 胡皆汉.光谱学与光谱分析, 2001, 21, 804.]
4. [4]
  (4) Leary, S. C;Winge, D. R. The Janus Face of Copper: Its Expanding Roles in Biology and the Pathophysiology of Disease. In Copper 06 in Sardinia, the Fifth International Copper Meeting on Copper and Related Metals in Biology, Alghero, Sardinia, Oct 14-18, 2006; Solioz, M., Thiele, D., Mercer, J., Eds.; EMBO Rep: London, 2007; p 224.
5. [5]
  (5) Brown, D. R.; Hafiz, F.; Glasssmith, L. L.; Wong, B. S.; Jones, I. M.; Clive, C.; Haswell, S. J. EMBO J. 2000, 19, 1180. doi: 10.1093/emboj/19.6.1180
6. [6]
  (6) Lin, C. J.; Huang, H. C.; Jiang, Z. F. Chemistry of Life 2009, 29, 696. [林昌君, 黄汉昌, 姜招峰. 生命的化学, 2009, 29, 696.]
7. [7]
  (7) Zhang, Y.; Zhu, J. M.; Liu, C. L. Acta Pharm. Sin. 2012, 47, 399. [张勇,竹俊苗, 刘长林. 药学学报, 2012, 47, 99.]
8. [8]
  (8) Wang, C. J.; Li, Y.; Yang, X. Y.; Lin, L. Acta Phys. -Chim. Sin. 2007, 23, 305. [王朝杰,李永, 杨新宇,林丽.物理化学学报, 2007, 23, 305.]
9. [9]
  (9) Li, Y. J.; Zhang, Q. Y.; Chen, Y. T. Chin. J. Inorg. Chem. 1991, 7, 82. [李跃进, 张启衍, 陈荣悌. 无机化学学报, 1991, 7, 82.]
10. [10]
  (10) Rulisek, L.; Havlas, Z. J. Am. Chem. Soc. 2000, 122, 10428. doi: 10.1021/ja001265g
11. [11]
  (11) Hoyau, S.; Ohanessian, G. J. Am. Chem. Soc. 1997, 119, 2016. doi: 10.1021/ja963432b
12. [12]
  (12) Remko, M.; Rode, B. M. J. Phys. Chem. A 2006, 110, 1960. doi: 10.1021/jp054119b
13. [13]
  (13) Rimola, A.; Santia , L. R.; Uglien , P.; Sodupe, M. J. Phys. Chem. B 2007, 111, 5740. doi: 10.1021/jp071071o
14. [14]
  (14) Jin, J.; Xu, X. T.; Cong, S. M.; Li, L.; Zhang, G. N.; Niu, S. Y. Acta Phys. -Chim. Sin. 2012, 28, 2549. [金品, 徐晓婷,丛盛美,李雷,张广宁, 牛淑云.物理化学学报, 2012, 28, 2549.]
15. [15]
  (15) Colaneri, M. J.; Vitali, J.; Peisach, J. J. Phys. Chem. A 2009, 113, 5700. doi: 10.1021/jp811249s
16. [16]
  (16) Lei, Q. P.; Amster, I. J. J. Am. Soc. Mass Spectrom. 1996, 7, 722. doi: 10.1016/1044-0305(96)80518-6
17. [17]
  (17) Cheng, W. X.; Chen, H. Y.; Zhang, Y. P.; Feng, Y.; Li, T. H.; Cao, H. Acta Chim. Sin. 2007, 65, 1956. [程伟贤, 陈鸿雁, 张义平,冯宇,李涛洪,曹槐.化学学报, 2007, 65, 1956.]
18. [18]
  (18) Nyberg, M.; Hasselstrom, J.; Karis, O.; Wassdahl, N.; Weinelt, M.; Nilsson, A.; Pettersson, L. G. M. J. Chem. Phys. 2000, 112, 5420. doi: 10.1063/1.481110
19. [19]
  (19) Fan, X. L.; Liu, Y.; Du, X. J.; Liu, C.; Zhang, C. Acta Phys. -Chim. Sin. 2013, 29, 263. [范晓丽, 刘燕, 杜秀娟, 刘崇,张超.物理化学学报, 2013, 29, 263.]
20. [20]
  (20) Shoeib, T.; Hopkinson, A. C.; Siu, K. W. M. J. Phys. Chem. B 2001, 105, 12399.
21. [21]
  (21) Rai, S.; Kumar, N. V. S.; Singh, H. Bull. Mater. Sci. 2012, 35, 291. doi: 10.1007/s12034-012-0314-6
22. [22]
  (22) Marino, T.; Russo, N.; Toscano, M. J. Phys. Chem. B 2003, 107, 2588. doi: 10.1021/jp027063j
23. [23]
  (23) Moision, R. M.; Armentrout, P. B. J. Phys. Chem. A 2006, 110, 3933. doi: 10.1021/jp060230l
24. [24]
  (24) Wang, C. J.; Cai, Y. P.; Huang, X. H.; Wei, T. Acta Phys. -Chim. Sin. 2011, 27, 352. [王朝杰, 蔡跃飘, 黄旭慧,卫涛.物理化学学报, 2011, 27, 352.]
25. [25]
  (25) Sun, X. L.; Jin, Q.; Wang, Y. N.; Cai, Y. P.; Wang, C. J. Acta Phys. -Chim. Sin. 2014, 30, 1071. [孙晓玲,金芩,王燕妮, 蔡跃飘, 王朝杰. 物理化学学报, 2014, 30, 1071.]
26. [26]
  (26) Liu, Y.; Zhao, J. J.; Li, F. Y.; Chen, Z. F. J. Comput. Chem. 2013, 34, 121. doi: 10.1002/jcc.23112
27. [27]
  (27) Jakubikova, E.; Rappe, A. K.; Bernstein, E. R. J. Phys. Chem. A 2006, 110, 9529.
28. [28]
  (28) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 09, Revision B.01; Gaussian Inc.: Wallingford, CT, 2010.
29. [29]
  (29) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303. doi: 10.1021/cr9603744
30. [30]
  (30) Marino, T.; Russo, N.; Toscano, M. J. Mass Spectrom. 2002, 37, 786.
31. [31]
  (31) Huang, M. L.; Huang, W. J. J. Quanzhou Norm. Univ. (Nat. Sci.) 2007, 25, 56. [黄妙龄, 黄文姣. 泉州师范学院学报(自然科学), 2007, 25, 56.]
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Computational Study on the Coordinate Systems of Proline with Cu, Cu+ and Cu2+

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通讯作者: 陈斌, bchen63@163.com

Computational Study on the Coordinate Systems of Proline with Cu, Cu⁺ and Cu²⁺