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Deprotonation of Indole Derivatives in Aqueous Cationic Surfactants
Author(s) -
Spreti Nicoletta,
Brinchi Lucia,
Di Profio Pietro,
Germani Raimondo,
Savelli Gianfranco,
Bunton Clifford A.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300555
Subject(s) - chemistry , deprotonation , aqueous solution , cationic polymerization , bromide , carboxylate , dissociation constant , alkyl , medicinal chemistry , inorganic chemistry , dissociation (chemistry) , indole test , ion , organic chemistry , biochemistry , receptor
Deprotonations of 5‐nitroindole, 1a , and its 2‐carboxylate ion, 2a , have been monitored in 0.01, 0.1, and 0.5 M NaOH in micellar solutions of cetyl trialkylammonium bromide, alkyl = Me, Et, n Pr, n Bu, CTABr, CTEABr, CTPABr, CTBABr. Extents of deprotonation (% f ) have been fitted using the pseudophase model of micellar effects with interionic competition described by ion exchange or by independent association constants. Both treatments indicate that base dissociation constants in dilute OH − are lower than in water by factors of ca. 3−11, and decrease with increasing bulk of the head groups, and that these factors increase modestly as the OH − concentration increases to 0.5 M . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)