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Title: A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds

Abstract

In this paper, the first example of a pseudo-bicyclic guanidinium ligand is reported. When bound to an anion, the N,N'-bis(2-pyridyl)guanidinium cation persistently adopts the planar α,α conformation featuring intramolecular N···H–N–H···N hydrogen bonds in the solid state, which facilitates crystallization of sulphate from aqueous mixtures of anions.

Authors:
 [1];  [2];  [3];  [3];  [3]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division; Univ. of Texas, Austin, TX (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division; Univ. of Tennessee, Knoxville, TN (United States)
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1286861
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
RSC Advances
Additional Journal Information:
Journal Volume: 5; Journal Issue: 130; Journal ID: ISSN 2046-2069
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Seipp, Charles A., Williams, Neil J., Bryantsev, Vyacheslav S., Custelcean, Radu, and Moyer, Bruce A. A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds. United States: N. p., 2015. Web. doi:10.1039/C5RA21864K.
Seipp, Charles A., Williams, Neil J., Bryantsev, Vyacheslav S., Custelcean, Radu, & Moyer, Bruce A. A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds. United States. doi:10.1039/C5RA21864K.
Seipp, Charles A., Williams, Neil J., Bryantsev, Vyacheslav S., Custelcean, Radu, and Moyer, Bruce A. Mon . "A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds". United States. doi:10.1039/C5RA21864K. https://www.osti.gov/servlets/purl/1286861.
@article{osti_1286861,
title = {A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds},
author = {Seipp, Charles A. and Williams, Neil J. and Bryantsev, Vyacheslav S. and Custelcean, Radu and Moyer, Bruce A.},
abstractNote = {In this paper, the first example of a pseudo-bicyclic guanidinium ligand is reported. When bound to an anion, the N,N'-bis(2-pyridyl)guanidinium cation persistently adopts the planar α,α conformation featuring intramolecular N···H–N–H···N hydrogen bonds in the solid state, which facilitates crystallization of sulphate from aqueous mixtures of anions.},
doi = {10.1039/C5RA21864K},
journal = {RSC Advances},
number = 130,
volume = 5,
place = {United States},
year = {2015},
month = {11}
}

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Cited by: 2 works
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Works referenced in this record:

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    Works referencing / citing this record:

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    Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
    journal, August 2015

    • Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
    • Angewandte Chemie International Edition, Vol. 54, Issue 36
    • DOI: 10.1002/anie.201506314

    Addressing Association Entropy by Reconstructing Guanidinium Anchor Groups for Anion Binding: Design, Synthesis, and Host–Guest Binding Studies in Polar and Protic Solutions
    journal, July 2008

    • Jadhav, Vinod D.; Herdtweck, Eberhardt; Schmidtchen, Franz P.
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    • DOI: 10.1002/chem.200702036

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    Reflections on the construction of anion receptors
    journal, December 2006


    Anion binding with urea and thiourea derivatives
    journal, July 2015

    • Blažek Bregović, Vesna; Basarić, Nikola; Mlinarić-Majerski, Kata
    • Coordination Chemistry Reviews, Vol. 295
    • DOI: 10.1016/j.ccr.2015.03.011

    Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    journal, September 1988

    • Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank
    • Chemical Reviews, Vol. 88, Issue 6
    • DOI: 10.1021/cr00088a005

    Artificial Organic Host Molecules for Anions
    journal, August 1997

    • Schmidtchen, Franz P.; Berger, Michael
    • Chemical Reviews, Vol. 97, Issue 5
    • DOI: 10.1021/cr9603845

    A Case for Molecular Recognition in Nuclear Separations: Sulfate Separation from Nuclear Wastes
    journal, June 2012

    • Moyer, Bruce A.; Custelcean, Radu; Hay, Benjamin P.
    • Inorganic Chemistry, Vol. 52, Issue 7
    • DOI: 10.1021/ic3016832

    Bis(alkylguanidinium) receptors for phosphodiesters: effect of counterions, solvent mixtures, and cavity flexibility on complexation
    journal, November 1993

    • Kneeland, Diane M.; Ariga, Katsuhiko; Lynch, Vincent M.
    • Journal of the American Chemical Society, Vol. 115, Issue 22
    • DOI: 10.1021/ja00075a021

    Anion Helicates:  Double Strand Helical Self-Assembly of Chiral Bicyclic Guanidinium Dimers and Tetramers around Sulfate Templates
    journal, January 1996

    • Sánchez-Quesada, Jorge; Seel, Christian; Prados, Pilar
    • Journal of the American Chemical Society, Vol. 118, Issue 1
    • DOI: 10.1021/ja953243d

    Intramolecular Hydrogen Bonding in Medicinal Chemistry
    journal, March 2010

    • Kuhn, Bernd; Mohr, Peter; Stahl, Martin
    • Journal of Medicinal Chemistry, Vol. 53, Issue 6
    • DOI: 10.1021/jm100087s

    Abiotic anion receptor functions. A facile and dependable access to chiral guanidinium anchor groups
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    • Kurzmeier, H.; Schmidtchen, F. P.
    • The Journal of Organic Chemistry, Vol. 55, Issue 12
    • DOI: 10.1021/jo00299a013

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