Acetalization and thioacetalization of cabonyl compounds: a case study based on global and local electrophilicity descriptors

Journal of Computational Chemistry
Ram Kinkar RoyKimihiko Hirao

Abstract

Acetalization of benzaldehyde and substituted benzaldehydes (containing both electron-donating and electron-withdrawing groups) is explained qualitatively on the basis of global electrophilicity descriptor, w, as proposed by Parr and coworkers. The generated values of w can explain qualitatively the preferential electrophilic addition, and hence, the yield of acetalization obtained in an earlier experimental study carried by Patel and coworkers. The present study also reveals that although both steric and electronic factors affect the yield, only later can be taken care of by w. In the case of a competitive formation of cyclic acetals and cyclic thioacetals from a reaction mixture containing p-hydroxybenzaldehyde, p-nitrobenzaldehyde, 1,2-ethanediol (i.e., glycol), and 1,2-ethanedithiol, the relative experimental yields could be explained from the difference of the global electrophilicity values between aldehydes and acetalizing agents in the same line of arguments of Maynard et al.

References

Oct 1, 1985·Proceedings of the National Academy of Sciences of the United States of America·W Yang, R G Parr
Sep 30, 1998·Proceedings of the National Academy of Sciences of the United States of America·A T MaynardD G Covell
Jul 6, 2002·The Journal of Organic Chemistry·Patricia PérezRenato Contreras
May 15, 2003·Chemical Reviews·P GeerlingsW Langenaeker
Jul 13, 2006·The Journal of Physical Chemistry. a·Ram Kinkar RoyKimihiko Hirao
Sep 1, 1986·Journal of the American Chemical Society·W Yang, W J Mortier

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Citations

Oct 29, 2008·Physical Chemistry Chemical Physics : PCCP·Soumen Saha, Ram Kinkar Roy
Jul 6, 2010·Physical Chemistry Chemical Physics : PCCP·Soumen SahaSourav Pal
Jun 17, 2010·Organic & Biomolecular Chemistry·Ramesh YellaBhisma K Patel
Nov 24, 2012·Journal of Computational Chemistry·Soumen SahaRam Kinkar Roy
Aug 20, 2010·Journal of Combinatorial Chemistry·Ramesh Yella, Bhisma K Patel
Dec 18, 2007·The Journal of Physical Chemistry. a·Priyanka Bagaria, Ram Kinkar Roy

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