A theoretical investigation of the interaction between substituted carbonyl derivatives and water: open or cyclic complexes?

Journal of Computational Chemistry
Asit K Chandra, Thérèse Zeegers-Huyskens

Abstract

The structures and binding energies of complexes between substituted carbonyl bases and water are the B3LYP/6-311++G(d,p) computational level. The calculations also include the proton affinity (PA) of the O of the C=O group, the deprotonation enthalpies (DPE) of the CH bonds along a natural bond orbital analysis. The calculations reveal that stable open C=O···H(w) O(w) as well as cyclic CH···O(w)H(w) ···O=C complexes are formed. The binding energies for the open complexes are linearly related to the PAs, whereas the binding energies for the cyclic complexes depend on both the PA and DPE. Different indicators of hydrogen bonds strength such as electron charge density, intramolecular and intermolecular hyperconjugation energy, occupation of orbitals, and charge transfer show significant differences between open and cyclic complexes. The contraction of the CH bond of the formyl group and the corresponding blue shift of the ν(CH) vibration are explained by the classical trans lone pair effect. In contrast, the elongation or contraction of the CH(3) group involved in the interaction with water results from the variation of the orbital interaction energies from the σ(CH) bonding orbital to the σ* and π* antibonding orbitals of the C=...Continue Reading

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Citations

Dec 6, 2012·Journal of Molecular Modeling·Wiktor ZierkiewiczThérèse Zeegers-Huyskens
Apr 4, 2013·The Journal of Physical Chemistry. a·Dipankar SutradharAsit K Chandra
Jun 10, 2017·Chemistry : a European Journal·Shaowei ShiXiaosong Wang
Mar 3, 2015·Journal of Computational Chemistry·Wiktor ZierkiewiczThérèse Zeegers-Huyskens
Nov 25, 2021·The Journal of Physical Chemistry. a·Nguyen Thi Thanh CucVu Thi Ngan

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