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Title: | Intramolecular hydrogen bond energy in polyhydroxy systems: A critical comparison of molecular tailoring and isodesmic approaches |
Authors: | Deshmukh, M M Suresh, C H Gadre, S R |
Keywords: | Hydrogen bond energies H-Bond energy Isodesmic reaction MTA Method Homodesmic reaction Propanetriol molecule Polyhydroxy system Molecular Tailoring Approach Butanetetraol Decitol |
Issue Date: | 19-Jul-2007 |
Publisher: | American Chemical Society, USA |
Citation: | Journal of Physical Chemistry 111(28):6472-6480;19 Jul 2007 |
Abstract: | The intramolecular hydrogen bond (H-bond) energies in several polyhydroxy systems are estimated using an isodesmic/homodesmic reaction approach as well as a molecular tailoring approach (MTA) [Deshmukh,M.M.Gadre, S.R. Baartolotti, L.J.J.Phys. Chem. A2006. 110.12519]. It is shown that the isodesmic/homodesmic reaction approach as advocated in the literature does not give true H-bond energy but includes the effect of strain energy due to the formation of a ring structure. Such a ring strain is duly accounted for in the MTA method. The isodesmic H-bond energies are found to be smaller than their MTA energy counterparts typically by the strain energy. The MTA is applied to decitol, a system with more than five different H-bonds for which an application of an appropriate isodesmic reaction is extremely difficult. It has been shown that the MTA method is able to predict not only the H-bond energies but also the trends in conformational energies for three different conformers of decitol studied in the present work. |
URI: | http://hdl.handle.net/123456789/52 |
Appears in Collections: | 2007 |
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