Journal article
Thermodynamic parameters including acid dissociation constants for bromochlorophenols (BCPs)
Journal of Chemical & Engineering Data, Vol.61(1), pp.160-172
2016
Abstract
This contribution reports standard gas-phase enthalpies of formation (ΔfH°298), entropies (S°298), and heat capacities (Cp°(T)) for all plausible 64 bromochlorophenols (BCPs) at the M062X meta hybrid level using a polarized basis set of 6-311+G(d,p). Isodesmic work reactions served to calculate the standard enthalpies of formation for all bromochlorophenol molecules and several bromochlorophenoxy radicals. Standard entropies and heat capacities comprise correction terms due to the treatment of O-H bonds as hindered rotors. Values of the bond dissociation enthalpies (BDHs) of O-H bonds, calculated for a selected series of bromochlorophenols, vary slightly with the change in the pattern and degree of halogenation of the phenyl ring. A thermodynamic cycle facilitated the estimation of pKa values, based on the calculated solvation and gas-phase deprotonation energies. We estimated the solvation energies of 19 out of 64 BCPs and their respective anions based on the integral equation formalism polarizable continuum model using optimized structures in the aqueous phase. Values of pKa decrease significantly from around 9 for monohalogenated to around 3 for pentahalogenated phenols.
Details
- Title
- Thermodynamic parameters including acid dissociation constants for bromochlorophenols (BCPs)
- Authors/Creators
- A. Saeed (Author/Creator)M. Altarawneh (Author/Creator)G. Hefter (Author/Creator)B.Z. Dlugogorski (Author/Creator)
- Publication Details
- Journal of Chemical & Engineering Data, Vol.61(1), pp.160-172
- Publisher
- American Chemical Society
- Grant note
- Grant ID: DP140104492
- Identifiers
- 991005541727907891
- Copyright
- © 2015 American Chemical Society.
- Murdoch Affiliation
- School of Veterinary and Life Sciences
- Language
- English
- Resource Type
- Journal article
UN Sustainable Development Goals (SDGs)
This output has contributed to the advancement of the following goals:
Source: InCites
Metrics
223 File views/ downloads
48 Record Views
InCites Highlights
These are selected metrics from InCites Benchmarking & Analytics tool, related to this output
- Citation topics
- 3 Agriculture, Environment & Ecology
- 3.60 Herbicides, Pesticides & Ground Poisoning
- 3.60.221 Persistent Organic Pollutants
- Web Of Science research areas
- Chemistry, Multidisciplinary
- Engineering, Chemical
- Thermodynamics
- ESI research areas
- Chemistry