Core Electron Binding Energy (CEBE) as Descriptors in Quantitative Structure–Activity Relationship (QSAR) Analysis of Cytotoxicities of a Series of Simple Phenols
Yuji Takahata, Masmoto Arakawa, Kimito Funatsu, Maria Cristina Andreazza Costa, Maximiliano Segala · QSAR & Combinatorial Science · 2006
Abstract Core Electron Binding Energies (CEBEs) of ring carbon atoms in 4‐X‐phenols were calculated using density‐functional theory with the scheme ΔEKS (PW86‐PW91)/TZP//HF/6‐31G*. The phenols show toxicity to fast growing cells. Using CEBEs of four distinguished carbon atoms in the phenyl ring and oxygen atom in OH of the phenols, the compounds were well separated and grouped by Principal Component Analysis (PCA). Using three out of the five CEBEs, together with σ+ and log P of the phenols as descriptor, we established a QSAR model with Partial Least Squares (PLS) regression which resulted in Q2=0.914. CEBE values when used together with traditionally used descriptors such as log P and σ+ turned out to be useful descriptors in modeling the activity (QSAR) of the compounds with PLS.