Abstract
2,4,6-Trimethylpyridine forms 1:1 complexes with methanol, 1,2-ethanediol, and water due to the O–H· · ·N bonds. The association energy of the complexes was calculated using MP2 and DFT methods. The complexes with 1,2-ethanediol and water aggregate in the liquid phase as a result of the O–H· · ·O bonds. In spite of the higher O–H· · ·N bond energy, the aggregation of the ethanediolic complexes is less pronounced than that of the aqueous ones. That is probably caused by the weaker induction effect due to the C–C chain separating the hydroxyl groups in the diol molecule. Aggregation is impossible in the methanolic system, because of the lack of proton-donating functional groups. Differences in the hydrogen bond energy and in the ability to aggregate are manifested in the volumetric properties of the mixtures.
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Acknowledgments
Acknowledgments The GAUSSIAN09 calculations were carried out in the Academic Computer Centre CYFRONET of the University of Science and Technology in Cracow, ACC CYFRONET AGH, Krakow, Poland, http://www.cyfronet.pl, under grant No. MNiSW/SGI3700/Uśląski/111/2007 and MNiSW/IBM_BC_HS21/Uśląski/111/2007.
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Open Access This is an open access article distributed under the terms of the Creative Commons Attribution Noncommercial License (https://creativecommons.org/licenses/by-nc/2.0), which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.
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Przybyła, A., Lodowski, P. & Marczak, W. Volumetric Properties of Binary Mixtures of 2,4,6-Trimethylpyridine with 1,2-Ethanediol, Methanol, and Water, and the Association Energies of the O–H· · ·N Bonded Complexes. Int J Thermophys 33, 692–706 (2012). https://doi.org/10.1007/s10765-011-1149-x
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DOI: https://doi.org/10.1007/s10765-011-1149-x