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

doi:10.6023/cjoc201702012

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1757-1763.DOI: 10.6023/cjoc201702012 Previous Articles Next Articles

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C-H…O氢键驱动的1,2,3-三氮唑折叠体:评估分子间C-H…X^-(X=Cl,Br,I)和C-H…N氢键的稳定性

孙广军^a, 聂承斌^a, 赵新^a, 黎占亭^a,b

a. 中国科学院上海有机化学研究所有机功能分子合成与组装化学实验室上海 200032;
b. 复旦大学化学系上海 200433

收稿日期:2017-02-11 修回日期:2017-03-07 发布日期:2017-03-17
通讯作者: 赵新, 黎占亭 E-mail:xzhao@sioc.ac.cn;ztli@fudan.edu.cn
基金资助:
国家自然科学基金（Nos.21272042，21432004）资助项目.

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

Received:2017-02-11 Revised:2017-03-07 Published:2017-03-17
Contact: 10.6023/cjoc201702012 E-mail:xzhao@sioc.ac.cn;ztli@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21272042,21432004).

1. 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.PDF(839KB)

Abstract

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.

Key words: hydrogen bonding, foldamer, 1,2,3-triazole, alkyne, molecular recognition, non-covalent interaction

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(7): 1757-1763.

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C-H…O氢键驱动的1,2,3-三氮唑折叠体:评估分子间C-H…X^-(X=Cl,Br,I)和C-H…N氢键的稳定性

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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C-H…O氢键驱动的1,2,3-三氮唑折叠体:评估分子间C-H…X-(X=Cl,Br,I)和C-H…N氢键的稳定性

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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C-H…O氢键驱动的1,2,3-三氮唑折叠体:评估分子间C-H…X^-(X=Cl,Br,I)和C-H…N氢键的稳定性

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