The transfer of neutral molecules, ions and ionic species from water to benzonitrile; comparison with nitrobenzene

Abstract

Equations have been constructed for the transfer of 64 neutral solutes from water and from the gas phase to the solvent benzonitrile. The equations contain five descriptors and can be used to predict further values of the water-benzonitrile and gas-benzonitrile partition coefficients for a wide range of solutes. The water-benzonitrile equation has been extended to include ions and ionic species derived from acids by loss of a proton and bases by acceptance of a proton. Only two further descriptors are needed, one for anions and one for cations. A previous equation for transfer of neutral solutes from water to nitrobenzene has also been extended to include ions and ionic species. Comparison of the equations for transfer to benzonitrile and to nitrobenzene shows that the two solvents behave quite similarly, although benzonitrile as a solvent is a stronger hydrogen bond base.

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

“…The model that we have been using in our studies has been the Abraham solvation parameter model [2,[21][22][23][24][25][26], which allows one to describe solute transfer between two condensed phases (a biphasic aqueous-organic or organic-organic system) or solute transfer to a condensed phase from the vapor phase. During the past five years we have published Abraham model correlations for 11 additional organic solvents (e.g., diisopropyl ether [27], tributyl phosphate [28], 2-hexadecene [29,30], 1,9-decadiene [29,30], sulfolane [31], benzonitrile [32], ethylbenzene [33], o-xylene [34], m-xylene [34], p-xylene [34], 2-ethoxyethanol [35], and propylene glycol [36]) and several ionic liquids [37][38][39][40][41][42][43][44][45][46][47], as well as updating our existing correlations for hexane [48], heptane [48], octane [48], decane [48], isooctane [49], toluene [33], tetrahydrofuran [50], and 1,4-dioxane [50].…”

Descriptors for ions and ion-pairs for use in linear free energy relationships

“…We include in Table 1 coefficients in Eq. (12) for all other the solvents we have studied, including ethylene glycol [58], propylene carbonate [58], sulfolane [59] nitrobenzene [60], benzonitrile [60], tetrahydrofuran [61], and 1,2-propylene glycol [62]. In Table 2 are given descriptors for the ions we have studied [39].…”

“…Abraham, Acree and coworkers [39,[58][59][60][61][62] obtained equation coefficients for 26 water-solvent partition systems, as shown in Table 1. The coefficients c, e, s, a, b and v are the same as those for the equation for neutral compounds.…”

Abraham model correlations for describing solute transfer into anhydrous 1,2-propylene glycol for neutral and ionic species

“…[5][6][7][8][77][78][79][80] Since the coefficients c p, e p, s p, a p, b p and v p remain the same in equations for the partition of neutral species and ions from water to a particular solvent, we can take these coefficients as those in Equation (5) and need only to determine the extra coefficients j p + and j p -in order to develop an equation for the partition of ionic compounds from water to propylene glycol. This requires a knowledge of partition coefficients for ionic compounds for transfer from water to propylene glycol.…”