Citation: SUN Xiao-Ling, JIN Qin, WANG Yan-Ni, CAI Yue-Piao, WANG Chao-Jie. Interaction and Properties of Proline-Zn^2+/1+/0 Complexes[J]. Acta Physico-Chimica Sinica, ;2014, 30(6): 1071-1085. doi: 10.3866/PKU.WHXB201404151 shu

Interaction and Properties of Proline-Zn^2+/1+/0 Complexes

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

Received Date: 26 January 2014
Available Online: 15 April 2014
Fund Project:

The hybrid density functional theory (DFT) methods M062X and X3LYP with the TZVP and 6-311++G(2d, p)+LANL2DZ basis sets were used to calculate the complexes formed between fifteen proline (Pro) conformers and Zn^2+/1+/0. The geometrical structures, energetics, vibrational frequencies, and electronic structures were investigated in detail. We obtained 19, 21, and 24 stable complexes for Pro-Zn^2+/1+/0 at the four levels. The most stable Pro-Zn²⁺ structure was a four-membered ring with Zn²⁺ bound to both oxygen ends (OO) of the zwitterionic proline, and the next stable compound was a five-membered ring with Zn²⁺ coordinated to both the amino nitrogen and carbonyl oxygen (NO) of proline, but Zn⁺ showed opposite behavior. The relative energy difference and the deformation energy of coordinated Pro decreased gradually with a reduction in the charge number of Zn. The binding energy of the Pro-Zn^2+/1+/0 systems are in the -620 to -936, -139 to -325, and -1.5 to -22 kJ·mol^-1 ranges, respectively. The properties of the Pro-Zn²⁺ system were significantly different when using different methods and basis sets. Both cationic systems indicated some charge transfer from Pro to Zn. The energy difference values for the frontier orbitals of all the complexes are lower than those of the corresponding fragments.
- Proline,
- M062X,
- X3LYP,
- Zn atom,
- Zn ion
1. [1]
  
  (1) Huang, L. P.; Tepaamorndech, S. Mol. Aspects Med. 2013, 34, 548. doi: 10.1016/j.mam.2012.05.008
2. [2]
  (2) Scheers, N. Nutrients 2013, 5, 957. doi: 10.3390/nu5030957
3. [3]
  (3) Garriga-Canut, M.; Agustin-Pavón, C.; Herrmann, F.; Sánchez, A.; Dierssen, M.; Fillat, C.; Isalan, M. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, E3136.
4. [4]
  (4) Lakatos, A.; Gyurcsik, B.; Nagy, N. V.; Csendes, Z.; Wéber, E.; Fülöp, L.; Kiss, T. Dalton Trans. 2012, 41, 1713. doi: 10.1039/c1dt10989h
5. [5]
  (5) Shan, S. S.; Yan, C.; Xu, L. Acta Phys. -Chim. Sin. 2013, 29, 2630. [单升升, 闫超,徐亮.物理化学学报, 2013, 29, 2630.] doi: 10.3866/PKU.WHXB201310302
6. [6]
  (6) Zhu, G. P.; Teng, M. K.; Wang, Y. Z. Prog. Biotechnol. 2000, 20, 48. [朱国萍,滕脉坤, 王玉珍. 生物工程进展, 2000, 20, 48.]
7. [7]
  (7) Cárcamo, J. J.; Aliaga, A. E.; Clavijo, E.; Garrido, C.; Gómez-Jeria, J. S.; Campos-Vallette, M. M. J. Raman Spectrosc. 2012, 43, 750. doi: 10.1002/jrs.3092
8. [8]
  (8) Daně?ek, P.; Kapitán, J.; Baumruk, V.; Bednárová, L.; Kopeck , V., Jr.; Bou?, P. J. Chem. Phys. 2007, 126, 224513. doi: 10.1063/1.2738065
9. [9]
  (9) Isaac, M.; Latour, J. M.; Sénèque, O. Chem. Sci. 2012, 3, 3409. doi: 10.1039/c2sc21029k
10. [10]
  (10) Siddiqui, Z. N.; Farooq, F. Catal. Sci. Technol. 2011, 1, 810. doi: 10.1039/c1cy00110h
11. [11]
  (11) Kofoed, J.; Machuqueiro, M.; Reymond, J. L.; Darbre, T. Chem. Commun. 2004, 1540.
12. [12]
  (12) Khalafi-Nezhad, A.; Sarikhani, S.; Shahidzadeh, E. S.; Panahi, F. Green Chem. 2012, 14, 2876. doi: 10.1039/c2gc35765h
13. [13]
  (13) Yang, H.; Wong, M. W. Org. Biomol. Chem. 2012, 10, 3229. doi: 10.1039/c2ob06993h
14. [14]
  (14) Venkatesan, G.; Anandha Babu, G.; Ramasamy, P.; Chandramohan, A. J. Mol. Struct. 2013, 1033, 121. doi: 10.1016/j.molstruc.2012.08.019
15. [15]
  (15) Kale, S. S.; Kotmale, A. S.; Dutta, A. K.; Pal, S.; Rajamohanan, P. R.; Sanjayan, G. J. Org. Biomol. Chem. 2012, 10, 8426. doi: 10.1039/c2ob26132d
16. [16]
  (16) Hernández, R.; Rodríguez, R.; Martínez, J. D.; Araujo, M. L.; Brito, F.; Lubes, G.; Rodríguez, M.; Hernández, L.; Lubes, V. J. Sol. Chem. 2012, 41, 1103. doi: 10.1007/s10953-012-9867-7
17. [17]
  (17) Garden, J. A.; Kennedy, A. R.; Mulvey, R. E.; Robertson, S. D. Dalton Trans. 2011, 40, 11945. doi: 10.1039/c1dt11430a
18. [18]
  (18) Qian, X.; Sun, P. P.; Ding, J. G.; Li, B. L.; Li, H. Y. J. Mol. Struct. 2013, 1031, 175. doi: 10.1016/j.molstruc.2012.07.016
19. [19]
  (19) Allen, W. D.; Czinki, E.; Császár, A. G. Chem. Eur. J. 2004, 10, 4512. doi: 10.1002/chem.200400112
20. [20]
  (20) Li, X. J.; Zhong, Z. J.; Wu, H. Z. J. Mol. Model. 2011, 17, 2623. doi: 10.1007/s00894-011-0957-z
21. [21]
  (21) Rogalewicz, F.; Ohanessian, G.; Gresh, N. J. Comput. Chem. 2000, 21, 963. doi: 10.1002/1096-987X(200008)21:11<963::AID-JCC6>3.0.CO;2-3
22. [22]
  (22) Ai, H. Q.; Bu, Y. X.; Han, K. L. J. Chem. Phys. 2003, 118, 10973. doi: 10.1063/1.1575192
23. [23]
  (23) Ai, H. Q.; Yang, A. B.; Li, Y. G. Acta Phys. -Chim. Sin. 2008, 24, 1047. [艾洪奇, 杨爱彬,李允刚. 物理化学学报, 2008, 24, 1047.] doi: 10.3866/PKU.WHXB20080623
24. [24]
  (24) Remko, M.; Fitz, D.; Rode, B. M. J. Phys. Chem. A 2008, 112, 7652. doi: 10.1021/jp801418h
25. [25]
  (25) Rulšíek, L.; Havlas, Z. J. Am. Chem. Soc. 2000, 122, 10428. doi: 10.1021/ja001265g
26. [26]
  (26) Tjörnhammar, R.; Edholm, O. J. Chem. Phys. 2010, 132, 205101. doi: 10.1063/1.3428381
27. [27]
  (27) Liu, W. M.; Liu, J. T.; Leng, H. X.; Zhu, Z. G. J. Mol. Sci. 2001, 17, 247. [刘伟明, 刘巨涛,冷红霞,朱志国.分子科学学报, 2001, 17, 247.]
28. [28]
  (28) Marino, T.; Russo, N.; Toscano, M. J. Phys. Chem. B 2003, 107, 2588. doi: 10.1021/jp027063j
29. [29]
  (29) Martínez-Magadán, J. M.; Ramírez-Solís, A.; Novaro, O. Chem. Phys. Lett. 1991, 186, 107. doi: 10.1016/0009-2614(91)80199-8
30. [30]
  (30) Ahmadi, M. S.; Fattahi, A. Sci. Iran. 2011, 18, 1343. doi: 10.1016/j.scient.2011.09.015
31. [31]
  (31) 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.] doi: 10.3866/PKU.WHXB20110232
32. [32]
  (32) 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.] doi: 10.1016/S1872-1508(07)60024-2
33. [33]
  (33) Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101. doi: 10.1063/1.2370993
34. [34]
  (34) Hargis, J. C.; Schaefer, H. F.; Houk, K. N.;Wheeler, S. E. J. Phys. Chem. A 2010, 114, 2038. doi: 10.1021/jp911376p
35. [35]
  (35) Liu, Y.; Zhao, J. J.; Li, F. Y.; Chen, Z. F. J. Comput. Chem. 2013, 34, 121. doi: 10.1002/jcc.23112
36. [36]
  (36) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299. doi: 10.1063/1.448975
37. [37]
  (37) David, R. L. CRC Handbook of Chemistry and Physics, 84th ed.; CRC Press Inc.: NewYork, 2003; p 10-178.
38. [38]
  (38) Jakubikova, E.; Rappe, A. K.; Bernstein, E. R. J. Phys. Chem. A 2006, 110, 9529.
39. [39]
  (39) Sun, T.; Wang, Y. B. Acta Phys. -Chim. Sin. 2011, 27, 2553. [孙涛, 王一波. 物理化学学报, 2011, 27, 2553.] doi: 10.3866/PKU.WHXB20111017
40. [40]
  (40) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.01; Gaussian Inc.: Wallingford, CT, 2009.
41. [41]
  (41) Vázquez, M. V.; Martínez, A. J. Phys. Chem. A 2007, 111, 9931.
1. [1]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
2. [2]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
3. [3]
  Li Lin , Song-Lin Tian , Zhen-Yu Hu , Yu Zhang , Li-Min Chang , Jia-Jun Wang , Wan-Qiang Liu , Qing-Shuang Wang , Fang Wang . Molecular crowding electrolytes for stabilizing Zn metal anode in rechargeable aqueous batteries. Chinese Chemical Letters, 2024, 35(7): 109802-. doi: 10.1016/j.cclet.2024.109802
4. [4]
  Xiping Dong , Xuan Wang , Zhixiu Lu , Qinhao Shi , Zhengyi Yang , Xuan Yu , Wuliang Feng , Xingli Zou , Yang Liu , Yufeng Zhao . Construction of Cu-Zn Co-doped layered materials for sodium-ion batteries with high cycle stability. Chinese Chemical Letters, 2024, 35(5): 108605-. doi: 10.1016/j.cclet.2023.108605
5. [5]
  Jie Zhou , Quanyu Li , Xiaomeng Hu , Weifeng Wei , Xiaobo Ji , Guichao Kuang , Liangjun Zhou , Libao Chen , Yuejiao Chen . Water molecules regulation for reversible Zn anode in aqueous zinc ion battery: Mini-review. Chinese Chemical Letters, 2024, 35(8): 109143-. doi: 10.1016/j.cclet.2023.109143
6. [6]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
7. [7]
  Yunfei Shen , Long Chen . Gradient imprinted Zn metal anodes assist dendrites-free at high current density/capacity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100321-100321. doi: 10.1016/j.cjsc.2024.100321
8. [8]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
9. [9]
  Zihao Wang , Jing Xue , Zhicui Song , Jianxiong Xing , Aijun Zhou , Jianmin Ma , Jingze Li . Li-Zn alloy patch for defect-free polymer interface film enables excellent protection effect towards stable Li metal anode. Chinese Chemical Letters, 2024, 35(10): 109489-. doi: 10.1016/j.cclet.2024.109489
10. [10]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
11. [11]
  Yufeng Wu , Mingjun Jing , Juan Li , Wenhui Deng , Mingguang Yi , Zhanpeng Chen , Meixia Yang , Jinyang Wu , Xinkai Xu , Yanson Bai , Xiaoqing Zou , Tianjing Wu , Xianyou Wang . Collaborative integration of Fe-N_x active center into defective sulfur/selenium-doped carbon for efficient oxygen electrocatalysts in liquid and flexible Zn-air batteries. Chinese Chemical Letters, 2024, 35(9): 109269-. doi: 10.1016/j.cclet.2023.109269
12. [12]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
13. [13]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
14. [14]
  Xin Jiang , Han Jiang , Yimin Tang , Huizhu Zhang , Libin Yang , Xiuwen Wang , Bing Zhao . g-C₃N₄/TiO_2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415
15. [15]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
16. [16]
  Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2023.100309
17. [17]
  Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt₃M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188
18. [18]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
19. [19]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
20. [20]
  Feiyang Liu , Liuhong Song , Miaoyu Fu , Zhi Zheng , Gang Xie , Junlong Zhao . Tryptophan’s Employment Journey. University Chemistry, 2024, 39(9): 16-21. doi: 10.12461/PKU.DXHX202404037

Get Citation

PDF

XML

Metrics

PDF Downloads(545)
Abstract views(640)
HTML views(23)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Interaction and Properties of Proline-Zn2+/1+/0 Complexes

Metrics

通讯作者: 陈斌, bchen63@163.com

Interaction and Properties of Proline-Zn^2+/1+/0 Complexes