Solvent effects on the redox properties of ferrocenoyl-dipeptides

被引:28
作者
Baker, MV
Kraatz, HB [1 ]
Quail, JW
机构
[1] Univ Western Australia, Dept Chem, Crawley, WA 6907, Australia
[2] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
关键词
D O I
10.1039/b005125j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The preparation and characterization of the novel ferrocenoyl-dipeptides, Fc-Asp(OBzl)-Asp(OBzl)-OBzl (5), Fc-Asp(OBzl)-Glu(OEt)-OEt (6) and Fc-Asp(OBzl)-Cys(Bzl)-OMe (7) are reported. In addition, Fc-Asp(OBzl)-OBzl (4) and its free acid, Fc-Asp(OH)-OH (8), were prepared. A crystal structure determination of 8 revealed an extensive H-bonding network involving a solvent molecule and adjacent molecules of 8 and suggests that these complexes are able to form strong hydrogen bonds with solvent molecules. All compounds show reversible one-electron oxidations in solution. The half-wave potential is strongly influenced by the nature of the solvent and correlates with the hydrogen donor ability alpha of the Kamlet-Taft formalism.
引用
收藏
页码:427 / 433
页数:7
相关论文
共 50 条
[21]  
Johnson C. K., 1976, ORNL5138
[22]  
Jones J.H., 1991, CHEM SYNTHESIS PEPTI
[23]   REDOX CHEMISTRY OF SUBSTITUTED BENZENES - THE ONE-ELECTRON REDUCTION POTENTIALS OF METHOXY-SUBSTITUTED BENZENE RADICAL CATIONS [J].
JONSSON, M ;
LIND, J ;
REITBERGER, T ;
ERIKSEN, TE ;
MERENYI, G .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (43) :11278-11282
[24]   REDOX PROPERTIES OF 4-SUBSTITUTED ARYL METHYL CHALCOGENIDES IN WATER [J].
JONSSON, M ;
LIND, J ;
MERENYI, G ;
ERIKSEN, TE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (01) :67-70
[25]   Redox and acidity properties of alkyl- and arylamine radical cations and the corresponding aminyl radicals [J].
Jonsson, M ;
Wayner, DDM ;
Lusztyk, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (44) :17539-17543
[26]   LINEAR SOLVATION ENERGY RELATIONSHIPS .23. A COMPREHENSIVE COLLECTION OF THE SOLVATOCHROMIC PARAMETERS, PI-STAR, ALPHA AND BETA, AND SOME METHODS FOR SIMPLIFYING THE GENERALIZED SOLVATOCHROMIC EQUATION [J].
KAMLET, MJ ;
ABBOUD, JLM ;
ABRAHAM, MH ;
TAFT, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2877-2887
[27]   The structure and energetics of helix formation by short templated peptides in aqueous solution .2. Characterization of the helical structure of Ac-Hel(1)-Ala(6)-OH [J].
Kemp, DS ;
Allen, TJ ;
Oslick, SL ;
Boyd, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4240-4248
[28]   The structure and energetics of helix formation by short templated peptides in aqueous solution .3. Calculation of the helical propagation constant s from the template stability constants t/c for Ac-Hel(1)-Ala(n)-OH, n=1-6 [J].
Kemp, DS ;
Oslick, SL ;
Allen, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4249-4255
[29]   Synthesis and electrochemistry of ferrocenemethylamine and its conjugated acid. Crystal structure of ferrocenemethylammonium chloride [J].
Kraatz, HB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 579 (1-2) :222-226
[30]   The ferrocene moiety as a structural probe:: redox and structural properties of ferrocenoyl-oligoprolines Fc-Pron-OBzl (n=1-4) and Fc-Pro2-Phe-OBzl [J].
Kraatz, HB ;
Leek, DM ;
Houmam, A ;
Enright, GD ;
Lusztyk, J ;
Wayner, DDM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 589 (01) :38-49