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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:
Journal Article: 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. https://doi.org/10.1039/C5RA21864K
Seipp, Charles A., Williams, Neil J., Bryantsev, Vyacheslav S., Custelcean, Radu, and Moyer, Bruce A. 2015. "A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds". United States. https://doi.org/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},
url = {https://www.osti.gov/biblio/1286861}, journal = {RSC Advances},
issn = {2046-2069},
number = 130,
volume = 5,
place = {United States},
year = {Mon Nov 30 00:00:00 EST 2015},
month = {Mon Nov 30 00:00:00 EST 2015}
}

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Cited by: 8 works
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Works referenced in this record:

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Works referencing / citing this record:

Simple guanidinium motif for the selective binding and extraction of sulfate
journal, March 2017


Simple guanidinium motif for the selective binding and extraction of sulfate [Supplementary Data]
preprint, October 2017


Simple guanidinium motif for the selective binding and extraction of sulfate
dataset, October 2017