Design of New Alkylphenols with Theoretical Values of their Water/ Octanol Partition Coefficients
Fatogoma Diarrassouba *
Laboratoire de Thermodynamique et Physico-Chimie du Milieu (LTPCM), UFR-SFA, Université Nangui ABROGOUA 02 BP 801 Abidjan 02, Côte d’Ivoire and Unité de Formation et de Recherche Sciences et Technologies (UFR-ST), Université Alassane OUATTARA, 01 BP 18 Bouaké 01, Côte d’Ivoire.
Cheickna Cissé
African Center of Excellence in Bioinformatics and Data Sciences (ACE-B), University of Sciences, Techniques and Technologies of Bamako (USTTB), Hamdallaye ACE 200, BP: 32 06, Bamako, Mali.
Kafoumba Bamba
Laboratoire de Thermodynamique et Physico-Chimie du Milieu (LTPCM), UFR-SFA, Université Nangui ABROGOUA 02 BP 801 Abidjan 02, Côte d’Ivoire.
Nahossé Ziao
Laboratoire de Thermodynamique et Physico-Chimie du Milieu (LTPCM), UFR-SFA, Université Nangui ABROGOUA 02 BP 801 Abidjan 02, Côte d’Ivoire and Groupe Ivoirien de Recherches en Modélisation des Maladies (GIR2M), Côte d'Ivoire.
*Author to whom correspondence should be addressed.
Abstract
In our previous work, we established a predictive QSPR (Quantitative Structure-Property Relationship) model for the water/octanol partition coefficient, based on electronic energy (ET), LUMO (Lowest Unoccupied Molecular Orbital) energy, and the energy gap (ΔEgap). This model has been shown to be suitable for predicting properties of new alkylphenols falling within its applicability domain, with a 5% risk level. The present study, which builds upon that earlier work, aims to expand the database for this family of compounds by designing new alkylphenols that fit within the established model's applicability domain and by predicting their water/octanol partition coefficients. In this context, we designed a series of forty-two (42) new alkylphenols. All these molecules were optimized at the B3LYP/6-311G(d,p) level of theory, and vibrational frequencies were calculated at the same level. Water/octanol partition coefficients calculated for these molecules using the model indicate that they are all lipophilic. The formation reaction for these new compounds proceeds spontaneously, accompanied by heat release and a decrease in disorder.
Keywords: Design, alkylphenol, QSPR model, standard thermodynamic quantities of formation