A COMPARISON OF PROTON AFFINITIES OF NEUTRAL OXYGEN AND SULFUR IN CHELATING LIGANDS

被引:4
作者
JAMES, TL
KULA, RJ
机构
[1] Department of Chemistry, University of Wisconsin, Madison
关键词
D O I
10.1021/j100723a026
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 nuclear magnetic resonance chemical shift behaviors of the nonexchanging carbon-bonded proton resonances of various S-alkylthioacelic acids and alkoxyacetic acids were studied in aqueous solution as a function of solvent acidity to determine the relative proton affinities of the donor atoms in such chelating ligands. The relative electron-donating abilities, ascertained from the sites and sequences of protonation, were found to be in the order (Chemical Equation Presented) This order of proton affinity seems to reflect the relative contributions of these donor atoms to the stability of metal chelates for those metal ions with little tendency for the formation of dative π bonds. The suitability of internal references in the strongly acidic solutions used in this investigation was also studied.
引用
收藏
页码:634 / &
相关论文
共 21 条
[1]   PROTON RESONANCE SPECTRA + CONFORMATIONS OF PROLINES .3. HYDROXYPROLINE + ALLOHYDROXYPROLINE IN ACID + ALKALINE SOLUTION [J].
ABRAHAM, RJ ;
THOMAS, WA .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (OCT) :3739-&
[2]   NUCLEAR MAGNETIC RESONANCE STUDIES OF PROTONATION OF WEAK BASES IN FLUOROSULFURIC ACID .V. KETONES CARBOXYLIC ACIDS AND SOME OTHER OXYGEN BASES [J].
BIRCHALL, T ;
GILLESPI.RJ .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (05) :1045-&
[3]   SOLVENT EFFECTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA [J].
BUCKINGHAM, AD ;
SCHAEFER, T ;
SCHNEIDER, WG .
JOURNAL OF CHEMICAL PHYSICS, 1960, 32 (04) :1227-1233
[4]   CHEMICAL SHIFTS IN THE NUCLEAR MAGNETIC RESONANCE SPECTRA OF MOLECULES CONTAINING POLAR GROUPS [J].
BUCKINGHAM, AD .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1960, 38 (02) :300-307
[5]   CHEMICAL BONDS INVOLVING D-ORBITALS .1. [J].
CRAIG, DP ;
MACCOLL, A ;
NYHOLM, RS ;
ORGEL, LE ;
SUTTON, LE .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JAN) :332-353
[6]   CARBONIUM IONS .17. DIRECT OBSERVATION OF SATURATED + UNSATURATED ACYL CATIONS + THEIR EQUILIBRIA WITH PROTONATED ACIDS [J].
DENO, NC ;
PITTMAN, CU ;
WISOTSKY, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (20) :4370-&
[7]   IONIZATION OF ORGANIC COMPOUNDS .4. STUDIES OF ETHANOL AND ETHYL ETHER IN SULPHURIC ACID BY NUCLEAR MAGNETIC RESONANCE [J].
EDWARD, JT ;
WANG, IC ;
LEANE, JB .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (08) :1521-&
[8]  
FREEMAN HC, 1966, BIOCHEMISTRY COPPER, P84
[9]   APPLICATION OF NUCLEAR MAGNETIC RESONANCE TO THE STUDY OF ACID-BASE EQUILIBRIA [J].
GRUNWALD, E ;
LOEWENSTEIN, A ;
MEIBOOM, S .
JOURNAL OF CHEMICAL PHYSICS, 1957, 27 (03) :641-642