Intramolecular Hydrogen Bonding Appetency for Conformational Penchants in Oxalohydrazide Fluoro Derivatives: NMR, MD, QTAIM, and NCI Studies

The Journal of Physical Chemistry. a
A LakshmipriyaN Suryaprakash

Abstract

The conformational stability of synthesized diphenyloxalohydrazide and dibenzoyloxalohydrazide fluoro derivatives has been investigated by extensive NMR studies that are ascertained by various levels of theoretical calculations. Two-dimensional1H-19F HOESY NMR experiments revealed the close spatial proximity between two NMR-active nuclei, confirming the hydrogen bond (HB)-mediated interaction between them, further aiding in establishing the probable stable conformations of these molecules. The relaxed potential energy scan disclosed the energy-minimized most stable structure among the several possible multiple conformations, which is in concurrence with NMR interpretations. Atomistic molecular dynamics simulations have been employed to unequivocally establish the conformational stability and the nature of HB formation at varied temperatures. With the possibility of occurrence of a number of probable conformations, the percentage of occurrences of different types of HBs in them was determined by MD simulations. Their population analysis was carried out using a Boltzmann distribution, in addition to deriving their Gibbs free energies. The molecular interactions governing the stable conformations have not only been ascertained by ...Continue Reading

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Citations

Jul 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ben E SmithGregory S Tschumper
Mar 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ilya G Shenderovich, Gleb S Denisov
Apr 20, 2018·The Journal of Physical Chemistry. a·Robert E Rosenberg

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