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Issue 40, 2010
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N–H⋯F hydrogen bonds in fluorinated benzanilides: NMR and DFT study

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Abstract

Using 19F and 1H-NMR (with 14N decoupling) spectroscopic techniques together with density functional theoretical (DFT) calculations, we have investigated weak molecular interactions in isomeric fluorinated benzanilides. Simultaneous presence of through space nuclear spin–spin couplings (1hJN–H⋯F) of diverse strengths and feeble structural fluctuations are detected as a function of site specific substitution of fluorine atoms within the basic identical molecular framework. The transfer of hydrogen bonding interaction energies through space is established by perturbing their strengths and monitoring the effect on NMR parameters. Multiple quantum (MQ) excitation, up to the highest possible MQ orders of coupled protons, is utilized as a tool for accurate 1H assignments. Results of NMR studies and DFT calculations are compared with the relevant structural parameters taken from single crystal X-ray diffraction studies.

Graphical abstract: N–H⋯F hydrogen bonds in fluorinated benzanilides: NMR and DFT study

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Article information


Submitted
08 May 2010
Accepted
08 Jul 2010
First published
06 Sep 2010

Phys. Chem. Chem. Phys., 2010,12, 13232-13237
Article type
Paper

N–H⋯F hydrogen bonds in fluorinated benzanilides: NMR and DFT study

G. N. Manjunatha Reddy, M. V. Vasantha Kumar, T. N. Guru Row and N. Suryaprakash, Phys. Chem. Chem. Phys., 2010, 12, 13232
DOI: 10.1039/C0CP00492H

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