Anion Binding of One-, Two-, and Three-Armed Thiourea Receptors Examined via Photoelectron Spectroscopy and Quantum Computations

Evgeny V. Beletskiy; Xue Bin Wang; Steven R. Kass

doi:10.1021/acs.jpca.6b08438

Anion Binding of One-, Two-, and Three-Armed Thiourea Receptors Examined via Photoelectron Spectroscopy and Quantum Computations

Evgeny V. Beletskiy, Xue Bin Wang, Steven R. Kass

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Benzene rings substituted with 1-3 thiourea containing arms (1-3) were examined by photoelectron spectroscopy and density functional theory computations. Their conjugate bases and chloride, acetate, and dihydrogen phosphate anion clusters are reported. The resulting vertical and adiabatic detachment energies span 3.93-5.82 eV (VDE) and 3.65-5.10 (ADE) for the deprotonated species and 4.88-5.97 eV (VDE) and 4.45-5.60 eV (ADE) for the anion complexes. These results reveal the stabilizing effects of multiple hydrogen bonds and anionic host-guest interactions in the gas phase. Previously measured equilibrium binding constants in aqueous dimethyl sulfoxide for all three thioureas are compared to the present results, and cooperative binding is uniformly observed in the gas phase but only for one case (i.e., 3·H₂PO₄^-) in solution.

Original language	English (US)
Pages (from-to)	8309-8316
Number of pages	8
Journal	Journal of Physical Chemistry A
Volume	120
Issue number	42
DOIs	https://doi.org/10.1021/acs.jpca.6b08438
State	Published - Oct 27 2016

Bibliographical note

Funding Information:
Generous support from the National Science Foundation (CHE-1361766) and the Minnesota Supercomputer Institute for Advanced Computational Research are gratefully acknowledged

Publisher Copyright:
© 2016 American Chemical Society.

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

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title = "Anion Binding of One-, Two-, and Three-Armed Thiourea Receptors Examined via Photoelectron Spectroscopy and Quantum Computations",

abstract = "Benzene rings substituted with 1-3 thiourea containing arms (1-3) were examined by photoelectron spectroscopy and density functional theory computations. Their conjugate bases and chloride, acetate, and dihydrogen phosphate anion clusters are reported. The resulting vertical and adiabatic detachment energies span 3.93-5.82 eV (VDE) and 3.65-5.10 (ADE) for the deprotonated species and 4.88-5.97 eV (VDE) and 4.45-5.60 eV (ADE) for the anion complexes. These results reveal the stabilizing effects of multiple hydrogen bonds and anionic host-guest interactions in the gas phase. Previously measured equilibrium binding constants in aqueous dimethyl sulfoxide for all three thioureas are compared to the present results, and cooperative binding is uniformly observed in the gas phase but only for one case (i.e., 3·H2PO4-) in solution.",

author = "Beletskiy, {Evgeny V.} and Wang, {Xue Bin} and Kass, {Steven R.}",

note = "Funding Information: Generous support from the National Science Foundation (CHE-1361766) and the Minnesota Supercomputer Institute for Advanced Computational Research are gratefully acknowledged Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

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doi = "10.1021/acs.jpca.6b08438",

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AU - Beletskiy, Evgeny V.

AU - Wang, Xue Bin

AU - Kass, Steven R.

N1 - Funding Information: Generous support from the National Science Foundation (CHE-1361766) and the Minnesota Supercomputer Institute for Advanced Computational Research are gratefully acknowledged Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2016/10/27

Y1 - 2016/10/27

N2 - Benzene rings substituted with 1-3 thiourea containing arms (1-3) were examined by photoelectron spectroscopy and density functional theory computations. Their conjugate bases and chloride, acetate, and dihydrogen phosphate anion clusters are reported. The resulting vertical and adiabatic detachment energies span 3.93-5.82 eV (VDE) and 3.65-5.10 (ADE) for the deprotonated species and 4.88-5.97 eV (VDE) and 4.45-5.60 eV (ADE) for the anion complexes. These results reveal the stabilizing effects of multiple hydrogen bonds and anionic host-guest interactions in the gas phase. Previously measured equilibrium binding constants in aqueous dimethyl sulfoxide for all three thioureas are compared to the present results, and cooperative binding is uniformly observed in the gas phase but only for one case (i.e., 3·H2PO4-) in solution.

AB - Benzene rings substituted with 1-3 thiourea containing arms (1-3) were examined by photoelectron spectroscopy and density functional theory computations. Their conjugate bases and chloride, acetate, and dihydrogen phosphate anion clusters are reported. The resulting vertical and adiabatic detachment energies span 3.93-5.82 eV (VDE) and 3.65-5.10 (ADE) for the deprotonated species and 4.88-5.97 eV (VDE) and 4.45-5.60 eV (ADE) for the anion complexes. These results reveal the stabilizing effects of multiple hydrogen bonds and anionic host-guest interactions in the gas phase. Previously measured equilibrium binding constants in aqueous dimethyl sulfoxide for all three thioureas are compared to the present results, and cooperative binding is uniformly observed in the gas phase but only for one case (i.e., 3·H2PO4-) in solution.

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Anion Binding of One-, Two-, and Three-Armed Thiourea Receptors Examined via Photoelectron Spectroscopy and Quantum Computations

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