Stability and Characteristics of the Halogen Bonding Interaction in an Anion-Anion Complex: A Computational Chemistry Study

doi:10.1021/acs.jpcb.5b08139

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	Stability and Characteristics of the Halogen Bonding Interaction in an Anion-Anion Complex: A Computational Chemistry Study
	Wang, Guimin 2; Chen, Zhaoqiang 2; Xu, Zhijian2,3 ; Wang, Jinan 2; Yang, Yang 2; Cai, Tingting 2; Shi, Jiye 1; Zhu, Weiliang2
刊名	JOURNAL OF PHYSICAL CHEMISTRY B
	2016-02-04
卷号	120 期号:4 页码:610-620
ISSN号	1520-6106
DOI	10.1021/acs.jpcb.5b08139
文献子类	Article
英文摘要	Halogen bonding is the noncovalent interaction between the positively charged a-hole of organohalogens and nucleophiles. In reality, both the organohalogen and nucleophile could be deprotonated to form anions, which may lead to the vanishing of the a-hole and possible repulsion between the two anions. However, our database survey in this study revealed that there are halogen bonding-like interactions between two anions. Quantum mechanics calculations with small model complexes composed of halobenzoates and propiolate indicated that the anion-anion halogen bonding is unstable in vacuum but attractive in solvents. Impressively, the QM optimized halogen bonding distance between the two anions is shorter than that in a neutral system, indicating a possibly stronger halogen bonding interaction, which is verified by the calculated binding energies. Furthermore, natural bond orbital and quantum theory of atoms in molecule analyses also suggested stronger anion anion halogen bonding than that of the neutral one. Energy decomposition by symmetry adapted perturbation theory revealed that the strong binding might be attributed to large induction energy. The calculations on 4 protein ligand complexes from PDB by the QM/MM method demonstrated that the anion-anion halogen bonding could contribute to the ligands' binding affinity up to similar to 3 kcal/mol. Therefore, anion-anion halogen bonding is stable and applicable in reality.
资助项目	National Natural Science Foundation of China[81273435] ; National Natural Science Foundation of China[81302699] ; National High Technology Research and Development Program of China[2012AA01A305] ; China Postdoctoral Science Foundation[2014T70/111] ; State Key Laboratory of Drug Research[SIMM1501KF-07]
WOS关键词	ADAPTED PERTURBATION-THEORY ; RATIONAL DRUG DESIGN ; HYDROGEN-BONDS ; NONCOVALENT INTERACTIONS ; AB-INITIO ; CHARGE-DENSITY ; INTERMOLECULAR INTERACTIONS ; DIELECTRIC-CONSTANT ; MECHANICAL METHOD ; SERUM-ALBUMIN
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000369773100002
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276151]
专题	药物发现与设计中心中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Xu, Zhijian; Shi, Jiye; Zhu, Weiliang
作者单位	1.UCB Biopharma SPRL, Braine Lalleud, Belgium; 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Drug Discovery & Design Ctr, Shanghai 201203, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Wang, Guimin,Chen, Zhaoqiang,Xu, Zhijian,et al. Stability and Characteristics of the Halogen Bonding Interaction in an Anion-Anion Complex: A Computational Chemistry Study[J]. JOURNAL OF PHYSICAL CHEMISTRY B,2016,120(4):610-620.
APA	Wang, Guimin.,Chen, Zhaoqiang.,Xu, Zhijian.,Wang, Jinan.,Yang, Yang.,...&Zhu, Weiliang.(2016).Stability and Characteristics of the Halogen Bonding Interaction in an Anion-Anion Complex: A Computational Chemistry Study.JOURNAL OF PHYSICAL CHEMISTRY B,120(4),610-620.
MLA	Wang, Guimin,et al."Stability and Characteristics of the Halogen Bonding Interaction in an Anion-Anion Complex: A Computational Chemistry Study".JOURNAL OF PHYSICAL CHEMISTRY B 120.4(2016):610-620.