Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H ••• π interactions

被引：31
|
作者：
Huang, Guo-Bao [1 ,2 ,3 ]
Liu, Wei-Er [3 ]
Valkonen, Arto [4 ,5 ]
Yao, Huan [3 ]
Rissanen, Kari [4 ,5 ]
Jiang, Wei [3 ]
机构：
[1] Yulin Normal Univ, Coll Chem & Food Sci, Yulin 537000, Peoples R China
[2] Shenzhen Univ, Coll Chem & Environm Engn, Shenzhen 518060, Peoples R China
[3] South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Peoples R China
[4] Univ Jyvaskyla, Dept Chem, POB 3540014, Jyvaskyla, Finland
[5] Univ Jyvaskyla, Nanosci Ctr, POB 3540014, Jyvaskyla, Finland
来源：
CHINESE CHEMICAL LETTERS | 2018年 / 29卷 / 01期
基金：
芬兰科学院; 中国国家自然科学基金;
关键词：
Macrocycles; Aromatic hydrocarbon; Molecular recognition; Host-guest chemistry; Hydrogen bond; BIS-NAPHTHALENE; COMPLEXATION; MACROCYCLES; ENCAPSULATION; ENERGETICS; CAVITY; RINGS; WATER;
D O I：
10.1016/j.cclet.2017.07.005
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Molecular recognition of aromatic hydrocarbons by four endo-functionalized molecular tubes has been studied by H-1 NMR spectroscopy, computational methods, and single crystal X-ray crystallography. The binding selectivity is rationalized by invoking shape complementarity and dipole alignment. The non covalent interactions are proved to predominantly be C/N-H center dot center dot center dot pi interactions. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：91 / 94
页数：4
相关论文
共 47 条
  • [1] Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H…π interactions
    Guo-Bao Huang
    Wei-Er Liu
    Arto Valkonen
    Huan Yao
    Kari Rissanen
    Wei Jiang
    Chinese Chemical Letters, 2018, 29 (01) : 91 - 94
  • [2] Selective Recognition of Highly Hydrophilic Molecules in Water by Endo-Functionalized Molecular Tubes
    Huang, Guo-Bao
    Wang, Sheng-Hua
    Ke, Hua
    Yang, Liu-Pan
    Jiang, Wei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (44) : 14550 - 14553
  • [3] Selective Encapsulation of Neutral Molecules by endo-Functionalized Molecular Tubes
    Valkonen, Arto
    Jiang, Wei
    Rissanen, Kari
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2016, 72 : S386 - S386
  • [4] Molecular Recognition and Chirality Sensing of Epoxides in Water Using Endo-Functionalized Molecular Tubes
    Wang, Li-Li
    Chen, Zhao
    Liu, Wei-Er
    Ke, Hua
    Wang, Sheng-Hua
    Jiang, Wei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (25) : 8436 - 8439
  • [5] endo-Functionalized molecular tubes: selective encapsulation of neutral molecules in non-polar media
    Huang, Guobao
    Valkonen, Arto
    Rissanen, Kari
    Jiang, Wei
    CHEMICAL COMMUNICATIONS, 2016, 52 (58) : 9078 - 9081
  • [6] Selective Recognition of Highly Hydrophilic Molecules in Water by Endo-Functionalized Molecular Tubes (vol 138, pg 14550, 2016)
    Huang, Guo-Bao
    Wang, Sheng-Hua
    Ke, Hua
    Yang, Liu-Pan
    Jiang, Wei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) : 5446 - 5446
  • [7] C-H and N-H bond dissociation energies of small aromatic hydrocarbons
    Barckholtz, C
    Barckholtz, TA
    Hadad, CM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (03) : 491 - 500
  • [8] Benzimidazole scaffold as dipodal molecular cleft for swift and efficient naked eye fluoride ion recognition via preorganized N-H and aromatic C-H in aqueous media
    Jain, Anshu
    Gupta, Ragini
    Agarwal, Madhu
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2017, 56 (05): : 513 - 518
  • [9] Erratum: Selective recognition of highly hydrophilic molecules in water by endo-functionalized molecular tubes (Journal of the American Chemical Society (2016) 138:44 (14550−14553) DOI: 10.1021/jacs.6b09472)
    Huang, Guo-Bao
    Wang, Sheng-Hua
    Ke, Hua
    Yang, Liu-Pan
    Jiang, Wei
    Journal of the American Chemical Society, 2020, 142 (11):
  • [10] C-H Activation Guided by Aromatic N-H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes
    Gupta, Sreya
    Han, Junghoon
    Kim, Yongjin
    Lee, Soon W.
    Rhee, Young Ho
    Park, Jaiwook
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9094 - 9103
12345