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This special issue honors Professor Michael H. Abraham, and the many experimental and theoretical contributions that he made to solution chemistry during his prolific scientific career. Michael possessed a very keen understanding of how molecular interactions influenced chemical reaction rates and chemical, spectral, thermodynamic and transport properties. He is most noted for developing the Abraham general solvation parameter that describes solute transfer between two condensed phases, as well as solute transfer from the gas phase. The model was described in a 1993 paper published in Chemical Society Reviews [1], and to date has received more than 1,800 citations according to Web of Science [2]. The basic model has been used successfully to describe a wide range of important chemical, biological and pharmaceutical properties, including both water-to-organic solvent and gas-to-organic solvent partition coefficients [3], gas–liquid chromatographic [4] and high-performance liquid chromatographic retention data [5], enthalpies of solvation [6], limiting diffusion coefficients for ions and nonelectrolyte solutes in water and in organic solvents [7], blood-to-body tissue and air-to-body tissue partition coefficients [8], median lethal molar concentrations for aquatic toxicities [9], human skin permeability of ionic and molecular compounds [10], Draize eye scores and eye irritation thresholds [11], nasal pungency [12], odor detection thresholds [13], minimum alveolar concentration for anesthetic potency [14], and human intestinal absorption [15]. On two separate occasions Michael was named the recipient of the Ebert Prize [16], which is awarded to authors of a published scientific paper in the Journal of Pharmaceutical Sciences describing novel and original research with high probability of significantly impacting the pharmaceutical sciences.
Michael was not only an accomplished scientist, but a very kind and caring individual who was always willing to assist fellow scientists. I, and many other researchers, have been very fortunate to have collaborated with Michael on numerous research projects. I benefitted greatly from our collaborations which began back in 1997 when I received a handwritten letter from Michael asking me to send him measured solubilities for trans-stilbene dissolved in organic solvents of varying polarity and hydrogen-bonding character. At that time one factor limiting the applicability of the Abraham model was the availability of solute descriptor values. Michael used the solubility data to demonstrate the calculation of Abraham model solute descriptors. The computation methodology [17] that Michael proposed has been used many times in recent years to calculate solute descriptors of numerous pesticides, herbicides, high-energy explosives [18], medicinal compounds [19] and the zwitterionic forms of α-amino acids [20]. Calculated solute descriptor values, alone or in combination with experimental spectral data, have been used to examine for possible intramolecular hydrogen-bond formation in 2-substituted phenols [21, 22], hydroxyflavones [23], hydroxyisoflavones [23] and dihydroxyanthraquinones [24]. I did not realize at the time that this simple request would lead to a 23-year research collaboration that would result in the publication of more than 250 joint, peer-reviewed research articles.
Michael maintained an active research program long after his formal retirement. At the time of his death in January of 2021, he was actively working on various computational approaches for estimating Abraham model solute descriptors, on developing Abraham model correlations to describe the solubilizing properties of environmentally friendly, renewable organic solvents and on examining the transition states in the solvolysis of tert-butyl chloride, bromide and iodide [25]. His vast knowledge of science allowed him to tackle problems having chemical, pharmaceutical and environmental significance. The papers published in this special issue are written by several of Michael’s research collaborators, close friends, and others who have used his theoretical models, experimental methods and computational methodologies in their research work. Papers appearing in this issue utilize various aspects of Michael’s research, and are mainly focused on the predictive and descriptive applications of the Abraham general solvation parameter model, on the computation of Abraham model solute descriptors, and on achieving a more thorough understanding of solute–solvent molecular interactions.
References
Abraham, M.H.: Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev. 22, 73–83 (1993)
Clarivate Analytics’s Web of Science Core Collection. https://www.webofscience.com/wos/woscc/basic-search. Accessed 28 June 2022.
Abraham, M.H., Acree, W.E., Jr.: Gas-solvent and water-solvent partition of trans-stilbene at 298 K. J. Mol. Liq. 238, 58–61 (2017)
Abraham, M.H., Poole, C.F., Salwa, K.: Classification of stationary phases and other materials by gas chromatography. J. Chromatogr. A 842, 79–114 (1999)
Oumada, F.Z., Roses, M., Bosch, E., Abraham, M.H.: Solute-solvent interactions in normal-phase liquid chromatography: a linear free-energy relationships study. Anal. Chim. Acta 382, 301–308 (1999)
Lu, J.Z., Acree, W.E., Jr., Abraham, M.H.: Abraham model correlations for enthalpies of solvation of organic solutes dissolved in N,N-dimethylacetamide, 2-butanone and tetrahydrofuran (UPATED) at 298.15 K. Phys. Chem. Liq. 58, 675–692 (2020)
Abraham, M.H., Acree, W.E., Jr.: Limiting diffusion coefficients for ions and nonelectrolytes in solvents water, methanol, ethanol, propan-1-ol, butan-1-ol, octan-1-ol, propanone and acetonitrile at 298 K, analyzed using Abraham descriptors. J. Solution Chem. 48, 748–757 (2019)
Abraham, M.H., Ibrahim, A., Zhao, Y., Acree, W.E., Jr.: A data base for partition of volatile organic compounds and drugs from blood/plasma/serum to brain, and an LFER analysis of the data. J. Pharm. Sci. 95, 2091–2100 (2006)
Hoover, K.R., Acree, W.E., Jr., Abraham, M.H.: Chemical toxicity correlations for several fish species based on the Abraham solvation parameter model. Chem. Res. Toxicol. 18, 1497–1505 (2005)
Abraham, M.H., Martins, F.: Human skin permeation and partition: general linear free-energy relationship analyses. J. Pharm. Sci. 93, 1508–1523 (2004)
Abraham, M.H., Hassanisadi, M., Jalali-Heravi, M., Ghafourian, T., Cain, W.S., Cometto-Muniz, J.E.: Draize rabbit eye test compatibility with eye irritation thresholds in humans: a quantitative structure-activity relationship analysis. Toxicol. Sci. 76, 384–391 (2003)
Abraham, M.H., Sanchez-Moreno, R., Cometto-Muniz, J.E., Cain, W.S.: A quantitative structure–activity analysis on the relative sensitivity of the olfactory and the nasal trigeminal chemosensory systems. Chem. Senses 32, 711–719 (2007)
Abraham, M.H., Acree, W.E., Jr., Cometto-Muniz, J.E.: Descriptors for terpene esters from chromatographic and partition measurements: estimation of human odor detection thresholds. J. Chromatogr. A 1609, 460428/1-460428/5 (2020)
Abraham, M.H., Acree, W.E., Jr., Mintz, C., Payne, S.: Effect of anesthetic structure on inhalation anesthesia: implications for the mechanism. J. Pharm. Sci. 97, 2373–2384 (2008)
Zhao, Y.H., Le, J., Abraham, M.H., Hersey, A., Eddershaw, P.J., Luscombe, C.N., Boutina, D., Beck, G., Sherborne, B., Cooper, I., Platts, J.A.: Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure–activity relationship (QSAR) with the Abraham descriptors. J. Pharm. Sci. 90, 749–784 (2001)
Ebert Prize—Free Virtual Issue. https://jpharmsci.org/ebert-prize. Accessed 28 June 2022.
Abraham, M.H., Green, C.E., Acree, W.E., Jr., Hernandez, C.E., Roy, L.E.: Descriptors for solutes from the solubility of solids: trans-stilbene as an example. J. Chem. Soc. Perkin Trans. 2, 2677–2682 (1998)
Abraham, M.H., Acree, W.E., Jr., Liu, X.: Descriptors for high-energy nitro compounds; Estimation of thermodynamic, physicochemical and environmental properties. Prop. Explos. Pyrotech. 46, 267–279 (2021)
Liu, X., Acree, W.E., Jr., Abraham, M.H.: Descriptors for some compounds with pharmacological activity; calculation of properties. Int. J. Pharm. 617, 121597/1-121597/9 (2022)
Abraham, M.H., Acree, W.E., Jr.: Solvation descriptors for zwitterionic α-aminoacids; Estimation of water-solvent partition coefficients, solubilities, and hydrogen-bond acidity and hydrogen-bond basicity. ACS Omega 4, 2883–2892 (2019)
Abraham, M.H., Du, C.M., Platts, J.A.: Lipophilicity of the nitrophenols. J. Org. Chem. 65, 7114–7118 (2000)
Abraham, M.H., Abraham, R.J., Aliev, A.E., Tormena, C.F.: Is there an intramolecular hydrogen bond in 2-halophenols? A theoretical and spectroscopic investigation. Phys. Chem. Chem. Phys. 17, 25151–25159 (2015)
Abraham, M.H., Acree, W.E., Jr., Earp, C.E., Vladimirova, A., Whaley, W.L.: Studies on the hydrogen bond acidity, and other descriptors and properties for hydroxyflavones and hydroxyisoflavones. J. Mol. Liq. 208, 363–372 (2015)
Acree, W.E., Jr., Smart, K., Abraham, M.H.: Abraham model solute descriptors reveal strong intramolecular hydrogen bonding in 1,4-dihydroxyanthraquinone and 1,8-dihydroxyanthraquinone. Phys. Chem. Liq. 56, 416–420 (2018)
Abraham, M.H., Martins, F., Elvas-Leitao, R., Moreira, L.: Properties of the tert-butyl halide solvolysis transition states. Phys. Chem. Chem. Phys. 23, 3311–3320 (2021)
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Acree, W.E. Introduction to the Michael Abraham Special Issue. J Solution Chem 51, 971–973 (2022). https://doi.org/10.1007/s10953-022-01189-5
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DOI: https://doi.org/10.1007/s10953-022-01189-5