Influence of aqueous dimethyl sulfoxide on pyridoxine protonation and tautomerization

被引:5
|
作者
Gamov, G. A. [1 ]
Zavalishin, M. N. [1 ]
Khokhlova, A. Yu. [1 ]
Sharnin, V. A. [1 ,2 ]
机构
[1] Ivanovo State Univ Chem & Technol, Res Inst Thermodynam & Kinet Chem Proc, Ivanovo, Russia
[2] Russian Acad Sci, GA Krestov Inst Solut Chem, Ivanovo, Russia
基金
俄罗斯基础研究基金会;
关键词
Pyridoxine; Protonation constant; Tautomeric constant; Gibbs energy change of transfer; Binary solvent; Transmembrane transport; DRUG DISCOVERY; HYDROGEN-BONDS; WATER; EQUILIBRIA; NMR; DIMETHYLSULFOXIDE; PERMEABILITY; COPPER(II); STABILITY; COMPLEXES;
D O I
10.1016/j.molliq.2016.06.031
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
The constants of pyridoxine (vitamin B-6) protolytic and tautomeric equilibria were determined by means of potentiometry and spectrophotometry respectively in wide range of binary solvent (aqueous dimethyl sulfoxide) compositions. The free Gibbs energies of pyridoxine molecular and zwitterionic species transfer from water to aqueous DMSO were obtained using method of partition between immiscible phases. These results were employed for discussing the transmembrane transport capability of B-6 vitamin. The influence of mixed solvent composition on pyridoxine protonation was analyzed taking into account the reagents solvation data. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:457 / 462
页数:6
相关论文
共 50 条
  • [21] Features of light scattering in aqueous solutions of dimethyl sulfoxide
    M. N. Rodnikova
    Yu. A. Zakharova
    I. A. Solonina
    D. A. Sirotkin
    Russian Journal of Physical Chemistry A, 2012, 86 : 892 - 894
  • [22] REACTION OF SELENIUM WITH ACETYLENE IN AQUEOUS DIMETHYL-SULFOXIDE
    TROFIMOV, BA
    AMOSOVA, SV
    GUSAROVA, NK
    TARASOVA, OA
    VORONKOV, MG
    ZHURNAL ORGANICHESKOI KHIMII, 1975, 11 (10): : 2225 - 2226
  • [23] MECHANISMS OF NUCLEOPHILIC DISPLACEMENT IN AQUEOUS DIMETHYL SULFOXIDE SOLUTIONS
    FUCHS, R
    BLOOMFIELD, JJ
    MCCRARY, GE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (20) : 4281 - &
  • [24] Oxidation of Dimethyl Sulfoxide in Aqueous Solution Using Microbubbles
    Li, Pan
    Tsuge, Hideki
    Itoh, Keiko
    INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2009, 48 (17) : 8048 - 8053
  • [25] Features of light scattering in aqueous solutions of dimethyl sulfoxide
    Rodnikova, M. N.
    Zakharova, Yu. A.
    Solonina, I. A.
    Sirotkin, D. A.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2012, 86 (05) : 892 - 894
  • [26] ALKALINE HYDROLYSIS OF ETHYL BENZOATE IN AQUEOUS DIMETHYL SULFOXIDE
    ROBERTS, DD
    JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07): : 2039 - &
  • [27] Dielectric spectrum and structure of aqueous solutions of dimethyl sulfoxide
    E. S. Verstakov
    S. A. Korobkova
    T. A. Nosaeva
    Russian Chemical Bulletin, 2020, 69 : 255 - 259
  • [28] Photoreactions of p-quinones with dimethyl sulfide and dimethyl sulfoxide in aqueous acetonitrile
    Görner, H
    PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2006, 82 (01) : 71 - 77
  • [29] INFLUENCE OF DIMETHYL SULFOXIDE ON RADIATION SENSITIVITY OF CATALASE
    LOHMANN, W
    MOSS, AJ
    PERKINS, WH
    JOURNAL OF NUCLEAR MEDICINE, 1965, 6 (07) : 519 - &
  • [30] Macroscopic and Microscopic Protonation Equilibria of Some α-Amino Acids in Dimethyl Sulfoxide–Water Mixtures
    Alev Doğan
    Nazife Aslan
    Pınar E. Erden
    Esin Canel
    Esma Kılıç
    Journal of Solution Chemistry, 2015, 44 : 1705 - 1722