pKa prediction using group philicity.

Chemical Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India.
The Journal of Physical Chemistry A (Impact Factor: 2.78). 06/2006; 110(20):6540-4. DOI: 10.1021/jp055849m
Source: PubMed

ABSTRACT Acid-base dissociation constants (pK(a) values) are important in understanding the chemical, environmental and toxicological properties of molecules. Though various methods have been developed to predict pK(a) by experimental and theoretical models, prediction of pK(a) is still complicated. Hence, a new approach for predicting pK(a) using the group philicity concept has been attempted. Presence of known functional groups in a molecule is utilized as the most important indicator to predict pK(a). The power of this descriptor in describing pK(a) for the series of carboxylic acids, various substituted phenols, anilines, phosphoric acids, and alcohols is probed. Results reveal that the group electrophilicity is suitable for effectively predicting the pK(a) values.

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