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Halide anion discrimination by a tripodal hydroxylamine ligand in gas and condensed phases.

  • Author(s): Cheisson, Thibault
  • Jian, Jiwen
  • Su, Jing
  • Eaton, Teresa M
  • Gau, Michael R
  • Carroll, Patrick J
  • Batista, Enrique R
  • Yang, Ping
  • Gibson, John K
  • Schelter, Eric J
  • et al.
Abstract

Electrospray ionization of solutions containing a tripodal hydroxylamine ligand, H3TriNOx ([((2-tBuNOH)C6H4CH2)3N]) denoted as L, and a hydrogen halide HX: HCl, HBr and/or HI, yielded gas-phase anion complexes [L(X)]- and [L(HX2)]-. Collision induced dissociation (CID) of mixed-halide complexes, [L(HXaXb)]-, indicated highest affinity for I- and lowest for Cl-. Structures and energetics computed by density functional theory are in accord with the CID results, and indicate that the gas-phase binding preference is a manifestation of differing stabilities of the HX molecules. A high halide affinity of [L(H)]+ in solution was also demonstrated, though with a highest preference for Cl- and lowest for I-, the opposite observation of, but not in conflict with, what is observed in gas phase. The results suggest a connection between gas- and condensed-phase chemistry and computational approaches, and shed light on the aggregation and anion recognition properties of hydroxylamine receptors.

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