R. Schwarzenbach, R. Stierli, B. Folsom
1988
Citations
8
Influential Citations
128
Citations
Quality indicators
Journal
Environmental science & technology
Abstract
Acidity constants, UV/vis absorption maxima, aqueous solubilities, octanol/water partition constants and ratios, vapor pressures, and estimated Henry's law constants are reported and discussed for 17 mono- and dinitrophenols. For substituted 2-nitrophenols in which intramolecular hydrogen bonding between hydroxyl and nitro group is not affected by proximity effects, the acidity constant K/sub a/ can be estimated from the Hammett relationship pK/sub a/ = 7.23 - 2.59 ..sigma.. sigma/sub i/ /sup (-)/. For these nitrophenols, the aqueous activity coefficient ..gamma../sub w/ of the nondissociated species is approximately independent of solute concentration, and a good correlation between octanol/water partition constant K/sub ow/ and aqueous solubility of the liquid compound C/sub w//sup sat/(L) is found: log K/sub ow/ = -0.97 log C/sub w//sup sat/(L) - 0.04 (R = 0.98). In cases in which intramolecular hydrogen bonding is disturbed or impossible, due to solute-solute interactions, C/sub w//sup sat/(L) does not yield correct information on ..gamma../sub w/ at low concentrations. The electronic effect of substituents on the octanol/water partitioning behavior of the dissociated 2-nitrophenols can be reasonably quantified by using Hammett substituent constants.