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

doi:10.1002/qua.24925

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	Organic fluorines as halogen bond donors: Theoretical study and crystallographic evidence
	Wang, Yanhua 4; Tong, Jianying 4; Wu, Weihong 2,3; Xu, Zhijian1 ; Lu, Yunxiang 2,3
刊名	INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
	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
DOI	10.1002/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.
资助项目	National Natural Science Foundation of China[21473054]
WOS关键词	C-F ; DENSITY FUNCTIONALS ; ACTIVE-SITE ; CHEMISTRY ; DESIGN
WOS研究方向	Chemistry ; Mathematics ; Physics
语种	英语
出版者	WILEY
WOS记录号	WOS:000356016300004
内容类型	期刊论文
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.