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Tributyl‐ and Triphenyltin Benzoates, Phenylacetates, and Cinnamates as Anion Carriers: an Electrochemical Assessment Coupled to Structural NMR Studies and AM1 Calculations
Author(s) -
Tsagatakis John K.,
Chaniotakis Nikolas A.,
Jurkschat Klaus,
Damoun Said,
Geerlings Paul,
Bouhdid Abdeslam,
Gielen Marcel,
Verbruggen Ingrid,
Biesemans Monique,
Martins José C.,
Willem Rudolph
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990407)82:4<531::aid-hlca531>3.0.co;2-5
Subject(s) - chemistry , potentiometric titration , benzoates , chloride , cinnamates , selectivity , inorganic chemistry , titration , sulfonium , ion , organic chemistry , salt (chemistry) , catalysis
A series of tributyl and triphenyltin benzoates, phenylacetates, and cinnamates, with different electron‐withdrawing substituents, were evaluated for their selectivity as anion carriers and for their application in liquid‐membrane potentiometric ion‐selective electrodes. The tributyltin carboxylates exhibited good sensitivity and significant chloride selectivities, while the corresponding triphenyltin benzoates were much less active. The observed potentiometric response differences were related to Sn‐atom Lewis acidity, as assessed by binding constants of chloride to the tin carriers determined from 117 Sn‐NMR titration experiments and theoretical simulations of the resulting titration curves. The thermodynamic characteristics as well as the expected chloride‐carrier adducts in relation to starting substrates were analyzed theoretically by AM1 calculations.