Complex formation of native and hydroxypropylated cyclodextrins with benzoic acid in aqueous solution: Volumetric and 1H NMR study

被引:20
|
作者
Terekhova, Irina [1 ]
Kozbial, Malgorzata [2 ]
Kumeev, Roman [1 ]
Gierycz, Pawel [2 ]
机构
[1] Russian Acad Sci, Inst Solut Chem, Ivanovo 153045, Russia
[2] Polish Acad Sci, Inst Phys Chem, PL-01224 Warsaw, Poland
基金
俄罗斯基础研究基金会;
关键词
PARTIAL MOLAR VOLUME; INCLUSION COMPLEXES; BETA-CYCLODEXTRIN; ALPHA-CYCLODEXTRIN; CARBOXYLIC-ACIDS; THERMODYNAMIC PROPERTIES; CIRCULAR-DICHROISM; CONJUGATE BASES; WATER; TOPOGRAPHY;
D O I
10.1016/j.cplett.2011.08.074
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Novel data on complexation of benzoic acid by parent and hydroxypropylated cyclodextrins were obtained by densimetry and H-1 NMR. Formation of 1: 1 inclusion complexes was detected in most cases with the exception of hydroxypropyl-gamma-cyclodextrin, which is able to form 1: 2 complexes. The data demonstrated penetration of carboxylic group of benzoic acid inside macrocyclic cavity, its insertion into beta-cyclodextrin cavity being deeper. Binding constants and volumes of transfer were calculated and analyzed in terms of influence of cyclodextrin structure on binding mode and driving forces of interaction as well as on the complex stability. (C) 2011 Elsevier B. V. All rights reserved.
引用
收藏
页码:341 / 346
页数:6
相关论文
共 50 条
  • [41] Inclusion complexes of 2-phenoxyethanol and alkoxyethanols in cyclodextrins: an 1H NMR study
    Cristiano Andrade-Dias
    Brian J. Goodfellow
    Luís Cunha-Silva
    José J. C. Teixeira-Dias
    Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2007, 57 : 151 - 156
  • [42] Potentiometric, UV and 1H NMR study on the interaction of penicillin derivatives with Zn(II) in aqueous solution
    Cardiano, Paola
    Cigala, Rosalia Maria
    Crea, Francesco
    De Stefano, Concetta
    Giuffre, Ottavia
    Sammartano, Silvio
    Vianelli, Giuseppina
    BIOPHYSICAL CHEMISTRY, 2017, 223 : 1 - 10
  • [43] Concentration Measurement of Amino Acid in Aqueous Solution by Quantitative 1H NMR Spectroscopy with Internal Standard Method
    Taichi Yamazaki
    Sakae Eyama
    Akiko Takatsu
    Analytical Sciences, 2017, 33 : 369 - 373
  • [44] Concentration Measurement of Amino Acid in Aqueous Solution by Quantitative 1H NMR Spectroscopy with Internal Standard Method
    Yamazaki, Taichi
    Eyama, Sakae
    Takatsu, Akiko
    ANALYTICAL SCIENCES, 2017, 33 (03) : 369 - 373
  • [45] Cyclodextrins binding to paeonol and two of its isomers in aqueous solution.: Isothermal titration calorimetry and 1H NMR investigations of molecular recognition
    Sun, De-zhi
    Li, Ling
    Qiu, Xiao-mei
    Liu, Min
    Yin, Bao-lin
    JOURNAL OF SOLUTION CHEMISTRY, 2006, 35 (11) : 1537 - 1549
  • [46] Cyclodextrins Binding to Paeonol and Two of Its Isomers in Aqueous Solution. Isothermal Titration Calorimetry and 1H NMR Investigations of Molecular Recognition
    De-zhi Sun
    Ling Li
    Xiao-mei Qiu
    Min Liu
    Bao-lin Yin
    Journal of Solution Chemistry, 2006, 35 : 1537 - 1549
  • [47] Chiral discrimination of the analgesic cizolirtine by using cyclodextrins:: A 1H NMR study on the solution structures of their host-guest complexes
    Redondo, J
    Blázquez, MA
    Torrens, A
    CHIRALITY, 1999, 11 (09) : 694 - 700
  • [48] 1H NMR studies of maltose, maltoheptaose, α-, β-, and γ-cyclodextrins, and complexes in aqueous solutions with hydroxy protons as structural probes
    Bekiroglu, S
    Kenne, L
    Sandström, C
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05): : 1671 - 1678
  • [49] 1H NMR characterization of complexation of Glutathione with silver and aluminum metals in aqueous solution
    Khan, Haroon
    Khan, Muhammad Khalid
    Ahmad, Tanveer
    Zaib, Muhammad Haris
    Zafar, Naheed
    Alghamdi, Mohammad A.
    MAIN GROUP CHEMISTRY, 2021, 20 (04) : 501 - 511
  • [50] Volumetric and 1H NMR spectroscopic studies of saccharides-calcium lactate interactions in aqueous solutions
    Amirchand, Khajuria Deepika
    Kaur, Sandeep
    Banipal, Tarlok S.
    Singh, Vickramjeet
    JOURNAL OF MOLECULAR LIQUIDS, 2021, 334