From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong C-H Hydrogen Bonds

doi:10.1002/chem.201100793

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	From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong C-H Hydrogen Bonds
	Ramabhadran, Raghunath O.1; Hua, Yuran 1; Li, Yong-jun 2; Flood, Amar H.1; Raghavachari, Krishnan 1
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2011-08-01
卷号	17 期号:33 页码:9123-9129
关键词	Anions Cyanide Binding Macrocycles Molecular Modeling Receptors
ISSN号	0947-6539
DOI	10.1002/chem.201100793
英文摘要	The multifaceted character of cyanide as an acceptor of hydrogen bonds from a receptor has been examined for the first time using electronic-structure theory and spectroscopic measurements (UV/Vis and NMR titrations). Motivated by the similar size and charge of the cyanide pseudohalide and the monoatomic chloride ion, strong interactions of cyanide with a rigid macrocyclic triazolophane receptor have been predicted by theory and confirmed by experimental findings. It was found that both anions bind with similar strength in the gas phase (computed) and in the solution phase (experimental) via C-H hydrogen bonds. Theoretical calculations predict that the heterodiatomic cyanide prefers to bind in the plane of the macrocycle along the north-south axis. Examination of the possible binding modes reveal low computed barriers for in-plane rotation. The predicted model is consistent with the experimental data. Overall, the binding of a molecular anion within the cavity of a triazolophane receptor has been characterized where the computed and experimental binding energies are consistent with the classification of cyanide as a pseudohalide in the context of supramolecular chemistry.
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000294706200017
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/71539]
专题	中国科学院化学研究所
通讯作者	Raghavachari, Krishnan
作者单位	1.Indiana Univ, Dept Chem, Bloomington, IN 47405 USA 2.Chinese Acad Sci, Inst Chem, CAS Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Ramabhadran, Raghunath O.,Hua, Yuran,Li, Yong-jun,et al. From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong C-H Hydrogen Bonds[J]. CHEMISTRY-A EUROPEAN JOURNAL,2011,17(33):9123-9129.
APA	Ramabhadran, Raghunath O.,Hua, Yuran,Li, Yong-jun,Flood, Amar H.,&Raghavachari, Krishnan.(2011).From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong C-H Hydrogen Bonds.CHEMISTRY-A EUROPEAN JOURNAL,17(33),9123-9129.
MLA	Ramabhadran, Raghunath O.,et al."From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong C-H Hydrogen Bonds".CHEMISTRY-A EUROPEAN JOURNAL 17.33(2011):9123-9129.