Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation

doi:10.6023/A1111211

Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (12): 1347-1354.DOI: 10.6023/A1111211 Previous Articles Next Articles

Special Topic

碱(土)金属离子与2-(3′-羟基-2′-吡啶基)苯并噁唑阳离子-π 复合物及其分子内质子转移过程的理论研究

易平贵, 刘峥军, 汪朝旭, 侯博, 于贤勇, 李筱芳

湖南科技大学化学化工学院理论化学与分子模拟省部共建教育部重点实验室分子构效关系湖南省普通高等学校重点实验室湘潭 411201

投稿日期:2011-11-21 修回日期:2012-04-20 发布日期:2012-04-20
通讯作者: 易平贵 E-mail:yipinggui@sohu.com
基金资助:
国家自然科学基金(Nos. 21172066, 20772027)湖南省自然科学基金(Nos. 10JJ4011, 11JJ2007)和湖南省高校创新平台开放基金(No. 09K081).

Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation

Yi Pinggui, Liu Zhengjun, Wang Zhaoxu, Hou Bo, Yu Xianyong, Li Xiaofang

Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Received:2011-11-21 Revised:2012-04-20 Published:2012-04-20
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172066, 20772027), Hunan Provincial Natural Science Foundation of China (Nos.10JJ4011, 11JJ2007), Scientific Research Fund of Hunan Provincial Education Department (No. 09K081).

The structures of 2-(3'-hydroxy-2'-pyridyl)benzoxazole (HPyBO) with alkali (or alkaline earth) metal ions (Li⁺, Na⁺, K⁺, Be²⁺, Mg²⁺ and Ca²⁺) were fully optimized at the 6-311++G(d,p) level by using B3LYP density functional theory and the binding energies were calculated at the same level. The result shows that the cation-π interaction between alkali (or alkaline earth) metal ions and HPyBO complexes are very strong, some of the interactions are even comparable to chemical bonding. The relative energies show that cation-π interaction can change the energy barrier of intramolecular proton transfer. When considering the solvent effect of water, the relative energies of isomers and the energy barrier of intramolecular proton transfer are changed to some extent. In addition, the properties at the BCPs (bond critical points) of intramolecular hydrogen bond in the complexes are also discussed.

Key words: density functional theory (DFT), cation-π interaction, intramolecular proton transfer, natural bond orbital (NBO), atoms in molecules (AIM)

Cite this article

Yi Pinggui, Liu Zhengjun, Wang Zhaoxu, Hou Bo, Yu Xianyong, Li Xiaofang. Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation[J]. Acta Chimica Sinica, 2012, 70(12): 1347-1354.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.

2 Berthier, G.; Savinelli, R.; Pullman, A. Theor. Chem. Acc.2000, 104, 78.

3 Adamo, C.; Berthier, G.; Savinelli, R. Theor. Chem. Acc.2004, 111, 176.

4 Dougherty, D. A. Science 1996, 271, 163.

5 Reddy, A. S.; Sastry, G. N. J. Phys. Chem. A 2005, 109,8893.

6 Liu, T.; Zhu, W.-L.; Gu, J.-D.; Shen, J.-H.; Luo, X.-M.; Chen, G.; Puah, C. M.; Silman, I.; Chen, K.-X.; Sussman, J. L.; Jiang, H.-L. J. Phys. Chem. A 2004, 108, 9400.

7 Zhu, W.-L.; Jiang, H.-L.; Puah, C. M.; Tan, X.-J.; Chen, K.-X.; Cao, Y.; Ji, R.-Y. J. Chem. Soc. Perkin Trans. 2 1999,2615.

8 Xu, Y.-C.; Shen, J.-H.; Zhu, W.-L.; Luo, X.-M.; Chen, K.-X.; Jiang, H.-L. J. Phys. Chem. B 2005, 109, 5945.

9 Zhu, W.-L.; Tan, X.-J.; Shen, J.-H.; Luo, X.-M.; Cheng, F.; Mok, P. C.; Ji, R.; Chen, K.-X.; Jiang, H.-L. J. Phys. Chem. A 2003, 107, 2296.

10 Felder, C.; Jiang, H.-L.; Zhu, W.-L.; Chen, K.-X.; Silman, I.; Botti, S. A.; Sussman, J. L. J. Phys. Chem. A 2001, 105,1326.

11 Vyas, N.; Ojha, A. K. Vib. Spectrosc. 2011, 56, 42.

12 Dinadayalane, T.; Hassan, A.; Leszczynski, J. J. Mol. Struct.2010, 976, 320.

13 Perraud, O.; Robert, V.; Gornitzka, H.; Martinez, A.; Dutasta, J.-P. Angew. Chem., Int. Ed. 2011, 51, 504.
14 Cheng, J.-G.; Luo, X.-M.; Yan, X.-H.; Li, Z.; Tang, Y.; Jiang, H.-L.; Zhu, W.-L. Sci. China, Ser. B 2008, 38, 269 (in Chinese). (程家高, 罗小民, 闫秀花, 李忠, 唐赟, 蒋华良, 朱维良, 中国科学(B 辑:化学), 2008, 38, 269.)
15 He, L.-Y.; Cheng, J.-G.; Wang, T.; Li, C.-M.; Gong, Z.; Liu, H.; Zeng, B.-B.; Jiang, H.-L.; Zhu, W.-L. Chem. Phys. Lett.2008, 462, 45.

16 Estarellas, C.; Frontera, A.; Qui?onero, D.; Deyà, P. M. Cent. Eur. J. Chem. 2010, 9, 25.
17 Estarellas, C.; Escudero, D.; Frontera, A.; Qui?onero, D.; Deyà, P. M. Theor. Chem. Acc. 2009, 122, 325.

18 Xu, W.-Z.; Ren, F.-D.; Ren, J.; Liu, S.-N.; Yue, Y.; Wang, W.-L.; Chen, S.-S. J. Mol. Model. 2010, 16, 615.

19 Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. J. Med. Chem. 2008, 51, 5135.

20 Zhang, C.-R.; Wang, L.; Ge, Y.-L.; Ju, X.-L. Chin. J. Org. Chem. 2007, 27, 1432 (in Chinese). (张成仁, 王柳, 葛燕丽, 巨修练, 有机化学, 2007, 27,1432.)
21 Xue, N. M.S. Thesis, Dalian University of Technology, Da lian, 2008 (in Chinese). (薛娜, 硕士论文, 大连理工大学, 大连, 2008.)

22 Um, S.-I. Dyes Pigm. 2007, 75, 185.

23 He, L. M.S. Thesis, Tianjin University, Tianjin, 2006 (in Chinese). (何莉莉, 硕士论文, 天津大学, 天津, 2006.)

24 Vázquez, S. R.; Rodríguez, M. C. R.; Mosquera, M.; Rodríguez-Prieto, F. J. Phys. Chem. A 2007, 111, 1814.

25 Yi, P.-G.; Peng, H.-L.; Yu, X.-Y.; Wang, Z.-X.; Tang, Z.-Q.; Wang, T. Acta Chim. Sinica 2009, 67, 276 (in Chinese). (易平贵, 彭洪亮, 于贤勇, 汪朝旭, 唐臻强, 王涛, 化学学报, 2009, 67, 276.)
26 Yi, P.-G.; Peng, H.-L.; Yu, X.-Y.; Li, X.-F.; Wang, Z.-X.; Wang, T.; Zhou, J. M. Acta Chim. Sinica 2010, 68, 875 (in Chinese). (易平贵, 彭洪亮, 于贤勇, 李筱芳, 汪朝旭, 王涛, 周继明, 化学学报, 2010, 68, 875.)
27 Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.

28 Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.

29 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. .; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03, Pittsburgh, PA, Gaussian, Inc., Wallingford CT, 2003.

30 Bader, R. F. W. Chem. Rev. 1991, 91, 893.

31 Nicholas, J. B.; Hay, B. P.; Dixon, D. A. J. Phys. Chem. A1999, 103, 1394.

32 Tan, X.-J.; Zhu, W.-L.; Cui, M.; Luo, X.-M.; Gu, J.-D.; Silman, I.; Sussman, J. L.; Jiang, H.-L.; Ji, R.-Y.; Chen, K.-X. Chem. Phys. Lett. 2001, 349, 113.
33 Winter, M. Webelements Periodic Table (http://www.webelements.com/), The University of Sheffield and WebElements Ltd, England.

34 Tsuzuki, S.; Uchimaru, T.; Mikami, M. J. Phys. Chem. A2003, 107, 10414.

35 Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747.

36 Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873.

37 Lipkowski, P.; Grabowski, S. J.; Robinson, T. L.; Leszczynski, J. J. Phys. Chem. A 2004, 108, 10865.

38 Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett.1998, 285, 170.

[1]	Guanglong Huang, Xiao-Song Xue. Computational Study on the Mechanism of Chen’s Reagent as Trifluoromethyl Source [J]. Acta Chimica Sinica, 2024, 82(2): 132-137.
[2]	Wenchao Bi, Linfeng Zhang, Jian Chen, Ruixue Tian, Hao Huang, Man Yao. Lithiation Mechanism and Performance of Monoclinic ZnP₂ Anode Materials [J]. Acta Chimica Sinica, 2022, 80(6): 756-764.
[3]	Mu Weihua, Ma Yao, Fang Decai, Wang Rong, Zhang Haina. Computational Insights into the Diels-Alder-alike Reactions of 1-Iodo-2-Lithio-o-Carborane with Fulvenes [J]. Acta Chim. Sinica, 2018, 76(1): 55-61.
[4]	Chen Xin, Yan Huijun, Xia Dingguo. Germanium Nanotube as the Catalyst for Oxygen Reduction Reaction: Performance and Mechanism [J]. Acta Chim. Sinica, 2017, 75(2): 189-192.
[5]	Yang Yinuo, Zhang Qi, Shi Jing, Fu Yao. Mechanism Study of Mn(I) Complex-catalyzed Imines and Alkynes Dehydrogenation Coupling Reaction [J]. Acta Chim. Sinica, 2016, 74(5): 422-428.
[6]	Liu Dingjia, Yu Haizhu, Fu Yao. DFT Study on Mechanism of Ruthenium-catalyzed meta Sulfonation [J]. Acta Chimica Sinica, 2013, 71(10): 1385-1395.
[7]	Li Peng, Zeng Yi, Chen Jinping, Li Yingying, Li Yi. Synthesis and Photophysical Study of Dendrimers Modified with ESIPT Chromophore [J]. Acta Chimica Sinica, 2012, 70(15): 1611-1616.
[8]	Han Lizhi, Wang Zhuo, Hua Yingjie, Ren Aimin, Liu Yanling, Liu Pengjun. Optoelectronic Properties of 9,9-Bis-(3-(9-phenyl-carbazoyl))-2,7-dipyrenylfluorene [J]. Acta Chimica Sinica, 2012, 70(05): 579-584 .
[9]	Feng Changjun. Theoretical Studies on Quantitative Structure-Activity Relationship and Structural Modification for 3-Substituted Sulfur-5- (2-Hydroxyphenyl)-4H-1,2,4-Triazole Compounds [J]. Acta Chimica Sinica, 2012, 70(04): 512-518.
[10]	Hao Jing, Meng Lingpeng, Sun Zheng, Zheng Shijun, Zeng Yanli. Topological Studies on the π…π Interactions between OCS, CO₂, N₂O and Hydrocarbon [J]. Acta Chimica Sinica, 2012, 70(04): 377-384.
[11]	WANG Lei, LIANG Hao-Jun. Density Functional Theory for Polyelectrolyte Mixtures Adsorption on Uniformly Charged Planar Surface [J]. Acta Chimica Sinica, 2011, 69(23): 2773-2780.
[12]	WU Yang, FAN Cui-E, ZHANG Li-Na, KONG Yu-Xia. A Theoretical Investigation of Ionic Liquids Formed between Protonated betaine Cation and bis(trifluoromethylsulfonyl)imide Anion [J]. Acta Chimica Sinica, 2011, 69(22): 2682-2690.
[13]	YI Ping-Gui, ZHOU Ji-Ming, WANG Chao-Xu, YU Xian-Yong, LI Xiao-Fang, CHEN Jian, LIU Zheng-Jun. Theoretical Study of Excited State Proton Transfer of 2-Phenyl- benzotriazole Derivatives with Different Proton Donor [J]. Acta Chimica Sinica, 2011, 69(14): 1645-1653.
[14]	DU Song-Song, LI Chun-Rong, ZHAO Chun-Mei, WEI Ni, WANG Wen-Liang. Terminal Group Effects on Electronic Structure and Carrier Transport Property of Conjugated Bridge of Bithiophene and Benzodithiophene [J]. Acta Chimica Sinica, 2011, 69(10): 1151-1159.
[15]	LV Nai-Xia, XU Xin. Theoretical Study of NO_x/CO₂/H₂O Adsorption on BaO(001) Surface [J]. Acta Chimica Sinica, 2011, 69(10): 1264-1268.

碱(土)金属离子与2-(3′-羟基-2′-吡啶基)苯并噁唑阳离子-π 复合物及其分子内质子转移过程的理论研究

Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments