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A solid-state ^35/37Cl NMR study of a chloride ion receptor and a GIPAW-DFT study of chlorine NMR interaction tensors in organic hydrochlorides

Rebecca P. Chapman,^a Jennifer R. Hiscock,^b Philip A. Gale,^b David L. Bryce^a

^aDepartment of Chemistry and Centre for Catalysis Research and Innovation, University of Ottawa, 10 Marie Curie Private, Ottawa, ON K1N 6N5, Canada.

^bSchool of Chemistry, University of Southampton, Southampton SO17 1BJ, UK.

Published on the web 5 July 2011.

Canadian Journal of Chemistry, 2011, 89:(7) 822-834, 10.1139/v10-177

Abstract

The results of a ^35/37Cl solid-state nuclear magnetic resonance (SSNMR) study of the 1-butyl-3-methylimidazolium chloride complex of meso-octamethylcalix[4]pyrrole (1) are reported. Line shapes obtained from magic-angle-spinning and stationary powder samples collected at 9.4 and 21.1 T are analyzed to provide the ^35/37Cl quadrupolar tensor and chemical shift (CS) tensor and their relative orientation. The relatively high symmetry of the chloride ion coordination environment is manifested in the small value of the quadrupole coupling constant, C_Q(³⁵Cl) = 1.0 MHz. The isotropic chemical shift of 120 ppm (with respect to NaCl(s)) is at the upper edge of the typical range seen for organic hydrochlorides. Consideration of chemical shift anisotropy (span, Ω = 50 ppm) and non-coincidence of the quadrupolar and CS tensors were essential to properly simulate the experimental spectra. The utility of gauge-including projector-augmented wave density functional theory (GIPAW-DFT) calculations of chlorine quadrupolar and CS tensors in organic chlorides was explored by validation against available benchmark experimental data for solid amino acid hydrochlorides. The calculations are shown to systematically overestimate the value of the ³⁵Cl quadrupole coupling constant. Additional calculations on various hydrated and solvated models of 1 are consistent with a structure in which solvent and water of hydration are absent.

Keywords: solid-state NMR, octamethylcalix[4]pyrrole, quadrupolar coupling, chemical shift tensor, halogen NMR, solvates, ion binding, receptors

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