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Extending the semi-empirical PM6 method for carbon oxyacid pKa prediction to sulfonic acids: Application towards congener-specific estimates for the environmentally and toxicologically relevant C1 through C8 perfluoroalkyl derivatives

Sierra Rayne¹, Kaya Forest² & Ken J. Friesen¹

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1. University of Winnipeg, Winnipeg, Manitoba, Canada
2. Okanagan College, Penticton, British Columbia, Canada

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Document Type:

Manuscript

Date:

Received 05 March 2009 00:53 UTC; Posted 06 March 2009

Subjects:

Chemistry, Earth & Environment

Tags:

• sulfonic acids
• semi-empirical
• PM6 method
• perfluoroalkyl derivatives
• pKa
• estimation

Abstract:

A positive bias in the semi-empirical PM6 method for estimating pKa values of sulfonic acids was corrected by a correlation developed between non-adjusted PM6 pKa values and the corresponding experimentally obtained/estimated acidity constants for a range of representative alkyl, aryl, and halogen substituted sulfonic acids. Application of this correction to PM6 values allows for extension of this computational method to a new acid functional group.

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This document is licensed to the public under the Creative Commons Attribution 3.0 License

How to cite this document:

Rayne, Sierra, Forest, Kaya, and Friesen, Ken. Extending the semi-empirical PM6 method for carbon oxyacid pKa prediction to sulfonic acids: Application towards congener-specific estimates for the environmentally and toxicologically relevant C1 through C8 perfluoroalkyl derivatives. Available from Nature Precedings <http://hdl.handle.net/10101/npre.2009.2922.1> (2009)

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