Water soluble calix[4]arenes. A thermodynamic investigation of proton complex formation

被引:94
作者
Arena, Giuseppe [1 ]
Cali, Rosario [1 ]
Lombardo, Gaetano Giuseppe [2 ]
Rizzarelli, Enrico [1 ,2 ]
Sciotto, Domenico [1 ]
Ungaro, Rocco [3 ]
Casnati, Alessandro [3 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, Viale A Doria 8, I-95125 Catania, Italy
[2] CNR, Ist Studio Sostanze Nat Interesse Alimentare & Ch, Catania, Italy
[3] Univ Parma, Ist Chim Organ, I-43100 Parma, Italy
关键词
D O I
10.1080/10610279208027437
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thermodynamic parameters of protonation of calix[4]arene-p-tetra sulphonate were potentiometrically and calorimetrically determined in aqueous solution at 25 degrees C and I = 0.1 mol dm(-3) (NaNO3). These values were compared with literature findings. AW and AF values reveal that the penta-anion protonation is energetically costly. In this connection the role played by hydrogen bonding and the cone conformation stabilization are critically discussed. Proton formation constants of the calix[4]arene-p-tetrasulphonate-tetra-carboxylate derivative in the cone conformation were also potentiometrically determined under the same experimental conditions.
引用
收藏
页码:19 / 24
页数:6
相关论文
共 19 条
  • [1] PKA OF CALIXARENES AND ANALOGS IN NONAQUEOUS SOLVENTS
    ARAKI, K
    IWAMOTO, K
    SHINKAI, S
    MATSUDA, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (12) : 3480 - 3485
  • [2] Arduini A., 1984, J CHEM SOC CHEM COMM, P981
  • [3] NONLINEAR LEAST-SQUARES APPROACH TO THE REFINEMENT OF ALL PARAMETERS INVOLVED IN ACID-BASE TITRATIONS
    ARENA, G
    RIZZARELLI, E
    SAMMARTANO, S
    RIGANO, C
    [J]. TALANTA, 1979, 26 (01) : 1 - 14
  • [4] Barnes D., 1969, J CHEM SOC A, P2073
  • [5] SYNTHESIS OF WATER-SOLUBLE MOLECULAR RECEPTORS FROM CALIX[4]ARENES FIXED IN THE CONE CONFORMATION
    CASNATI, A
    TING, YH
    BERTI, D
    FABBI, M
    POCHINI, A
    UNGARO, R
    SCIOTTO, D
    LOMBARDO, GG
    [J]. TETRAHEDRON, 1993, 49 (43) : 9815 - 9822
  • [6] Christensen J.J., 1976, HANDBOOK OF PROTON I
  • [7] NOVEL LAYER STRUCTURE OF SODIUM CALIX[4]ARENESULFONATE COMPLEXES - A CLASS OF ORGANIC CLAY MIMICS
    COLEMAN, AW
    BOTT, SG
    MORLEY, SD
    MEANS, CM
    ROBINSON, KD
    ZHANG, HM
    ATWOOD, JL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (10): : 1361 - 1362
  • [8] COMPUTATIONAL STUDY OF THE STRUCTURAL, ENERGETICAL, AND ACID-BASE PROPERTIES OF CALIX[4]ARENES
    GROOTENHUIS, PDJ
    KOLLMAN, PA
    GROENEN, LC
    REINHOUDT, DN
    VANHUMMEL, GJ
    UGOZZOLI, F
    ANDREETTI, GD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4165 - 4176
  • [9] Gutsche C.D., 1989, ROYAL SOC CHEM
  • [10] Gutsche C.D., 1991, INCLUSION COMPOUNDS, V4