Real-time mechanistic monitoring of an acetal hydrolysis using ultrafast 2D NMR

被引:29
|
作者
Queiroz, Luiz H. K., Jr. [1 ,2 ]
Giraudeau, Patrick [3 ]
dos Santos, Fabiane A. B. [1 ]
de Oliveira, Kleber T. [1 ]
Ferreira, Antonio G. [1 ]
机构
[1] Univ Fed Sao Carlos UFSCar, Dept Quim, Lab Ressonancia Magnet Nucl, BR-13565905 Sao Carlos, SP, Brazil
[2] Univ Fed Goias, Inst Quim, Lab Ressonancia Magnet Nucl, Goiania, Go, Brazil
[3] Univ Nantes, CNRS, UMR 6230, Nantes, France
基金
巴西圣保罗研究基金会;
关键词
NMR; 1H; 13C; ultrafast NMR; NMR theoretical calculations; acetal hydrolysis; hemiacetal intermediate; SPECTROSCOPY; SENSITIVITY;
D O I
10.1002/mrc.3827
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ultrafast (UF) 2D NMR makes it possible to obtain a 2D NMR spectrum in less than a second. Here, UF-HSQC experiments are used for the real-time mechanistic study of an acetal hydrolysis at C-13 natural abundance, and it is possible to characterize the presence of the hemiacetal, an intermediate with a well-known short lifetime. The assignments are confirmed and rationalized by quantum calculations of H-1 and C-13 NMR chemical shifts and natural bonding orbital analysis. Copyright (c) 2012 John Wiley & Sons, Ltd.
引用
收藏
页码:496 / 501
页数:6
相关论文
共 50 条
  • [1] Real-time reaction monitoring by ultrafast 2D NMR on a benchtop spectrometer
    Gouilleux, Boris
    Charrier, Benoit
    Danieli, Ernesto
    Dumez, Jean-Nicolas
    Akoka, Serge
    Felpin, Francois-Xavier
    Rodriguez-Zubiri, Mireia
    Giraudeau, Patrick
    ANALYST, 2015, 140 (23) : 7854 - 7858
  • [2] Real-time monitoring of chemical transformations by ultrafast 2D NMR spectroscopy
    Gal, M
    Mishkovsky, M
    Frydman, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) : 951 - 956
  • [3] Real-time monitoring of chemical transformations by ultrafast 2D NMR spectroscopy
    Gal, Maayan
    Mishkovsky, Mor
    Frydman, Lucio
    Journal of the American Chemical Society, 2006, 128 (03): : 951 - 956
  • [4] In Situ Ultrafast 2D NMR Spectroelectrochemistry for Real-Time Monitoring of Redox Reactions
    Boisseau, Renaud
    Bussy, Ugo
    Giraudeau, Patrick
    Boujtita, Mohammed
    ANALYTICAL CHEMISTRY, 2015, 87 (01) : 372 - 375
  • [5] Monitoring Mechanistic Details in the Synthesis of Pyrimidines via Real-Time, Ultrafast Multidimensional NMR Spectroscopy
    Pardo, Zulay D.
    Olsen, Gregory L.
    Encarnacion Fernandez-Valle, Maria
    Frydman, Lucio
    Martinez-Alvarez, Roberto
    Herrera, Antonio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2706 - 2715
  • [6] Real-time separation of natural products by ultrafast 2D NMR coupled to on-line HPLC
    Queiroz Junior, Luiz H. K.
    Queiroz, Darlene P. K.
    Dhooghe, Liene
    Ferreira, Antonio G.
    Giraudeau, Patrick
    ANALYST, 2012, 137 (10) : 2357 - 2361
  • [7] Real-time benchtop NMR spectroscopy for the online monitoring of sucrose hydrolysis
    Soyler, Alper
    Bouillaud, Dylan
    Farjon, Jonathan
    Giraudeau, Patrick
    Oztop, Mecit H.
    LWT-FOOD SCIENCE AND TECHNOLOGY, 2020, 118
  • [8] Real-Time Monitoring of Cancer Cell Metabolism and Effects of an Anticancer Agent using 2D In-Cell NMR Spectroscopy
    Wen, He
    An, Yong Fin
    Xu, Wen Jun
    Kang, Keon Wook
    Park, Sunghyouk
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (18) : 5374 - 5377
  • [9] Real-Time 2D Microwave Differential Imaging for Temperature Monitoring
    Lee, Kwang-Jae
    Kim, Jang-Yeol
    Kim, Bo-Ra
    Jeon, Soon-Ik
    Kim, Nam
    Son, Seong-Ho
    2018 INTERNATIONAL SYMPOSIUM ON ANTENNAS AND PROPAGATION (ISAP), 2018,
  • [10] Real-time observation of multiexcitonic states in ultrafast singlet fission using coherent 2D electronic spectroscopy
    Bakulin, Artem A.
    Morgan, Sarah E.
    Kehoe, Tom B.
    Wilson, Mark W. B.
    Chin, Alex W.
    Zigmantas, Donatas
    Egorova, Dassia
    Rao, Akshay
    NATURE CHEMISTRY, 2016, 8 (01) : 16 - 23