Citation: Sun Guangjun, Nie Chengbin, Zhao Xin, Li Zhanting. Intramolecular C-H…O Hydrogen Bonding-Driven 1, 2, 3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1757-1763. doi: 10.6023/cjoc201702012 shu

Intramolecular C-H…O Hydrogen Bonding-Driven 1, 2, 3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding

Sun Guangjun ^a ,
Nie Chengbin ^a ,
Zhao Xin ^a,, ,
Li Zhanting ^a,b,,

a.
Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032
b.
Department of Chemistry, Fudan University, Shanghai 200433

Corresponding author: Zhao Xin, xzhao@sioc.ac.cn Li Zhanting, ztli@fudan.edu.cn
Received Date: 11 February 2017
Revised Date: 7 March 2017
Available Online: 17 July 2017
Fund Project: National Natural Science Foundation of China 21272042Project supported by the National Natural Science Foundation of China (Nos. 21272042, 21432004)National Natural Science Foundation of China 21432004

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1, 2, 3-Triazole aromatic oligomers are driven by intramolecular three-center C-H…O hydrogen bonding to form folded or helical secondary structures. This paper reports the assessment of their ability to form intermolecular C-H…Cl^- in CDCl₃ or C-H…N hydrogen bonding in CD₂Cl₂ by using ¹H NMR. It is revealed that the two kinds of intramolecular six-membered C-H…O hydrogen bondings of the backbones are both weakened by Cl^- through the formation of intermolecular C-H…Cl^- hydrogen bonding. In the presence of excess of Cl^-, the C-H…O hydrogen bonding on the N-1 side of the triazole units is, to a large extent, broken by intermolecular C-H…Cl^- hydrogen bonding, which induces the backbones to form another kind of more extended crescent secondary structures. Under similar conditions, excess of Br^- and I^- can also form similar intermolecular hydrogen bonding. It is also found that the inside-located N-2 and N-3 atoms of the triazole units of a 8-mer oligomer can also form weak intermolecular C-H…N hydrogen bonding with C-H atoms of the alkynyl units of several tri-and bi-alkynes, which is enhanced by the folded conformation of the oligomer through forcing the N-2 and N-3 atoms to arrange into a ring.
- hydrogen bonding,
- foldamer,
- 1, 2, 3-triazole,
- alkyne,
- molecular recognition,
- non-covalent interaction
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Intramolecular C-H…O Hydrogen Bonding-Driven 1, 2, 3-Trazole Foldamers:Assessment of Intermolecular C-H…X- (X=Cl, Br, I) and C-H…N Hydrogen Bonding

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通讯作者: 陈斌, bchen63@163.com

Intramolecular C-H…O Hydrogen Bonding-Driven 1, 2, 3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding