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Three centered hydrogen bonds of the type C=O...H(N)...X-C in diphenyloxamide derivatives involving halogens and a rotating CF3 group: NMR, QTAIM, NCI and NBO studies

Lakshmipriya, A and Chaudhari, Sachin Rama and Shahi, Abhishek and Arunan, E and Suryaprakash, N (2015) Three centered hydrogen bonds of the type C=O...H(N)...X-C in diphenyloxamide derivatives involving halogens and a rotating CF3 group: NMR, QTAIM, NCI and NBO studies. In: PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 17 (11). pp. 7528-7536.

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Official URL: http://dx.doi.org/10.1039/c4cp05917d

Abstract

The existence of three centered C=O...H(N)...X-C hydrogen bonds (H-bonds) involving organic fluorine and other halogens in diphenyloxamide derivatives has been explored by NMR spectroscopy and quantum theoretical studies. The three centered H-bond with the participation of a rotating CF3 group and the F...H-N intramolecular hydrogen bonds, a rare observation of its kind in organofluorine compounds, has been detected. It is also unambiguously established by a number of one and two dimensional NMR experiments, such as temperature perturbation, solvent titration, N-15-H-1 HSQC, and F-19-H-1 HOESY, and is also confirmed by theoretical calculations, such as quantum theory of atoms in molecules (QTAIM), natural bond orbital (NBO) and non-covalent interaction (NCI).

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Keywords: VARIABLE-TEMPERATURE NMR; SPIN-SPIN COUPLINGS; ORGANIC FLUORINE; MOLECULAR-DYNAMICS; SCALAR COUPLINGS; H-1-NMR SPECTRA; N-15 NMR; SPECTROSCOPY; CONFORMATION; COMPLEXES
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Division of Chemical Sciences > NMR Research Centre (Formerly Sophisticated Instruments Facility)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 24 Apr 2015 06:15
Last Modified: 24 Apr 2015 06:15
URI: http://eprints.iisc.ac.in/id/eprint/51402

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