Abstract
Ketones are one of the most common functional groups, and ketone-containing compounds are essential in both the nature and the chemical sciences. As such, the acidities (pKa) of ketones provide valuable information for scientists to screen for biological activities, to determine physical properties or to study reaction mechanisms. Direct measurements of pKa of ketones are not readily available due to their extremely weak acidity. Hence, a quantitative structure-property relationship (QSPR) model that can predict the acidities of ketones and their acidity order is highly desirable. The establishment of an acidity scale in dimethyl sulfoxide (DMSO) solution by Bordwell et al. made such an effort possible. By utilizing the pKa values of forty-eight ketones determined in DMSO as the training set, a QSPR model for predicting acidities of ketones was built by stepwise multiple linear regression analysis. The established model showed statistical significance and predictive power (r2 = 0.91, q2 = 0.86, s = 1.42). Moreover, the QSPR model also gave reasonable acidity predictions for five ketones in an external prediction set that were not included in the model generation phase (r2 = 0.92, s = 1.618). Overall, the reported QSPR model for predicting acidities of ketones provides a useful tool for both biologists and chemists in understanding the biophysical properties and reaction rates of different classes of ketones.
Highlights
Ketones play a crucial role in nature
Ketones are important in both biochemistry and organic chemistry, and information about their pKa properties will be beneficial for both biologists and chemists
A quantitative structureproperty relationship (QSPR) model which can be used to predict the acidities of ketones is highly desirable
Summary
Ketones play a crucial role in nature. Metabolism of carbohydrates, fatty acids and amino acids in humans and most vertebrates generates acetone, acetoacetate and beta-hydroxybutyrate, which are known as ketone bodies in biochemistry. Acetoacetate and betahydroxybutyrate are important fuels for many tissues. It was reported that acetoacetate contributes over 90% to the energy required for respiration in the sheep heart, 85% in the sheep kidney cortex and 74% in the sheep diaphragm [1]. Ketone bodies are found to have therapeutic values for neurological diseases such as Alzheimer’s disease [2,3] and Parkinson’s disease [3, 4]. It was reported that monoacetoacetin (glycerol monoacetoacetate) has the potential to decrease growth of human gastric cancer cells [7]
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