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Temperature-dependent acid dissociation constants (K/sub a/,. delta. H/sub a/,. delta. S/sub a/) for a series of nitrogen-substituted hydroxamic acids in aqueous solution

Journal Article · · J. Org. Chem.; (United States)
DOI:https://doi.org/10.1021/jo00346a005· OSTI ID:5288287
;

The acid dissociation constants (K/sub a/) of a series of eight substituted N-phenylacetohydroxamic acids, CH/sub 3/C(O)N(OH)C/sub 6/H/sub 4/X (X = H,4-CH/sub 3/, 4-Cl, 4-I, 3-I, 3-CN, 4-CN, 4-C(O)CH/sub 3/), have been determined in aqueous solution (I = 2.0) for a range of temperatures. The pK/sub a/ data at 25 /sup 0/C exhibit a small variation with the substituent X in the direction expected according to their Hammett substituent constants (p approx. = 0.1). These small variations in pK/sub a/ values are due to compensating trends in ..delta..H/sub a/ and ..delta..S/sub a/, which show significant variation with substituent. These results are discussed in terms of the substituent's influence on hydroxamate anion-slvent interactions and the relative influence on pK/sub a/ of a substituted phenyl group attached to the C or N end of the hydroxamate moiety.

Research Organization:
Duke Univ., Durham, NC
OSTI ID:
5288287
Journal Information:
J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:7; ISSN JOCEA
Country of Publication:
United States
Language:
English

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AMINES
AQUEOUS SOLUTIONS
CHEMICAL ANALYSIS
CHEMICAL REACTIONS
DATA
DISPERSIONS
DISSOCIATION
ENTHALPY
ENTROPY
EXPERIMENTAL DATA
HYDROXAMIC ACIDS
HYDROXY COMPOUNDS
INFORMATION
MEDIUM TEMPERATURE
MIXTURES
NITRO COMPOUNDS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHYSICAL PROPERTIES
QUANTITATIVE CHEMICAL ANALYSIS
REAGENTS
RESONANCE
SOLUTIONS
TEMPERATURE DEPENDENCE
THERMODYNAMIC PROPERTIES