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Organic fluorines as halogen bond donors: Theoretical study and crystallographic evidence

文献类型：期刊论文

作者Wang, Yanhua4; Tong, Jianying4; Wu, Weihong2,3; Xu, Zhijian1; Lu, Yunxiang2,3
刊名INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
出版日期2015-07-15
卷号115期号:14页码:884-890
关键词organic fluorines halogen bond donors M06-2x substituents crystal structures
ISSN号0020-7608
DOI10.1002/qua.24925
文献子类Article
英文摘要Organic fluorines usually cannot act as halogen bond donors, as a result of the extreme electronegativity and least polarizability of the fluorine atom. However, when the electronegative ability of the substituents bound to the carbon atom is very strong, organic fluorines do show positive electrostatic potentials (ESPs) along the CF bond and thus can form halogen bonds with electron donors. In this work, the effects of six different substituents, i.e., NO2, CF3, CN, COOH, CHO, and CCH, on the ESPs of the F atom were studied using the M06-2x method. When two or three substituents with very strong electron-withdrawing ability, such as NO2 and CN, are linked to the C atom, positive ESPs take place on the outermost portion of the F atom. However, the ESPs remain negative along the CF bond with the introduction of relatively weak electron-withdrawing substituents, irrespective of the number of the subsituents. In addition, some complexes between fluorinated molecules with positive ESPs on the F atom and NH3 were calculated, to characterize the structural and energetic features of these specific halogen bonds. Finally, some crystal structures extracted from the Cambridge Structural Database were selected to provide experimental evidence of these interactions involving the CF bond. The results presented in this work are very important for the modern definition of halogen bonding as well as for the development of pharmaceuticals and a wide range of functional material. (c) 2015 Wiley Periodicals, Inc.
WOS关键词C-F ; DENSITY FUNCTIONALS ; ACTIVE-SITE ; CHEMISTRY ; DESIGN
资助项目National Natural Science Foundation of China[21473054]
WOS研究方向Chemistry ; Mathematics ; Physics
语种英语
WOS记录号WOS:000356016300004
出版者WILEY
源URL[http://119.78.100.183/handle/2S10ELR8/276468]  
专题药物发现与设计中心
通讯作者Wang, Yanhua
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, Shanghai 201203, Peoples R China
2.E China Univ Sci & Technol, Dept Chem, Shanghai 200237, Peoples R China;
3.E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;
4.Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou 310015, Zhejiang, Peoples R China;
推荐引用方式
GB/T 7714		 Wang, Yanhua,Tong, Jianying,Wu, Weihong,et al. Organic fluorines as halogen bond donors: Theoretical study and crystallographic evidence[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2015,115(14):884-890.
APA Wang, Yanhua,Tong, Jianying,Wu, Weihong,Xu, Zhijian,&Lu, Yunxiang.(2015).Organic fluorines as halogen bond donors: Theoretical study and crystallographic evidence.INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,115(14),884-890.
MLA Wang, Yanhua,et al."Organic fluorines as halogen bond donors: Theoretical study and crystallographic evidence".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 115.14(2015):884-890.

入库方式： OAI收割

来源：上海药物研究所

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