Synthesis and Characterization of Calixarene Tetraethers: An Exercise in Supramolecular Chemistry for the Undergraduate Organic Laboratory

被引:11
|
作者
Debbert, Stefan L. [1 ]
Hoh, Bradley D. [1 ]
Dulak, David J. [1 ]
机构
[1] Lawrence Univ, Dept Chem, 711 East Boldt Way, Appleton, WI 54911 USA
基金
美国国家科学基金会;
关键词
Second-Year Undergraduate; Laboratory Instruction; Hands-On Learning/Manipulatives; Organic Chemistry; Alkylation; Phenols; Conformational Analysis; Noncovalent Interactions; NMR Spectroscopy; COMPLEXATION; KINETICS;
D O I
10.1021/acs.jchemed.5b00641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this experiment for an introductory undergraduate organic chemistry lab, students tetraalkylate tert-butylcalix[4]arene, a bowl-shaped macrocyclic oligophenol, and examine the supramolecular chemistry of the tetraether product by proton nuclear magnetic resonance (NMR) spectroscopy. Complexation with a sodium ion reduces the conformational mobility of the macrocycle through host-guest interactions, greatly simplifying the H-1 NMR spectrum of the macrocycle and providing an excellent example of geminal coupling between the diastereotopic protons of the methylene bridges. By dealing explicitly with the organic chemistry of large molecules and host-guest complementarity, this experiment provides a useful pedagogical bridge from small-molecule organic chemistry to the biochemistry of macromolecules such as enzymes.
引用
收藏
页码:372 / 375
页数:4
相关论文
共 50 条
  • [21] CHEMICAL REDUCTION IN UNDERGRADUATE ORGANIC CHEMISTRY LABORATORY
    KUSHNER, AS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (NSEP): : 10 - &
  • [22] Integration of Computational Chemistry into the Undergraduate Organic Chemistry Laboratory Curriculum
    Esselman, Brian J.
    Hill, Nicholas J.
    JOURNAL OF CHEMICAL EDUCATION, 2016, 93 (05) : 932 - 936
  • [23] LABORATORY EXERCISE FOR ORGANIC-CHEMISTRY
    SANDS, RD
    JOURNAL OF CHEMICAL EDUCATION, 1975, 52 (11) : 732 - 732
  • [24] POLYMER SYNTHESIS IN UNDERGRADUATE ORGANIC LABORATORY
    SORENSON, WR
    JOURNAL OF CHEMICAL EDUCATION, 1965, 42 (01) : 8 - &
  • [25] Synthesis of capsaicin for undergraduate organic laboratory
    George, Kathryn D.
    Jensen, Dell W., Jr.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [26] Gas Chromatography-Mass Spectrometry Analysis of Cannabis: Undergraduate Organic Chemistry Laboratory Exercise
    Lynch, Hailey N.
    Authement, Claire Chaz
    Maczko, Autumn
    Parker, Miranda
    Beaty, Kaylan
    Pathiranage, Anuradha Liyana
    JOURNAL OF CHEMICAL EDUCATION, 2023, 100 (03) : 1303 - 1312
  • [27] An Enzyme Kinetics Experiment for the Undergraduate Organic Chemistry Laboratory
    Olsen, Robert J.
    Olsen, Julie A.
    Giles, Greta A.
    JOURNAL OF CHEMICAL EDUCATION, 2010, 87 (09) : 956 - 957
  • [28] Greening the Wittig reaction for the undergraduate organic chemistry laboratory
    MacKay, James A.
    Wetzel, Nicholas R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [29] Course based undergraduate research in the organic chemistry laboratory
    Hunsen, Mo
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [30] SAFETY TRAINING FOR UNDERGRADUATE ORGANIC-CHEMISTRY LABORATORY
    MOON, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 18 - CHAS