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

Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S.; Custelcean, Radu; Moyer, Bruce A.

doi:10.1039/C5RA21864K

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

Journal Article · 29 November 2015 · RSC Advances

DOI: https://doi.org/10.1039/C5RA21864K · OSTI ID:1286861

Seipp, Charles A. ^[1]; Williams, Neil J. ^[2]; Bryantsev, Vyacheslav S. ^[3]; Custelcean, Radu ^[3]; Moyer, Bruce A. ^[3]

Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division; Univ. of Texas, Austin, TX (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division; Univ. of Tennessee, Knoxville, TN (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1286861

Journal Information:: RSC Advances, Journal Name: RSC Advances Journal Issue: 130 Vol. 5; ISSN 2046-2069

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (25)

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Cited By (5)

Synthesis of Bicyclic and Tricyclic Chiral Guanidinium Salts by an Intramolecular Alkylation Approach: Synthesis of Bicyclic and Tricyclic Chiral Guanidinium Salts by an Intramolecular Alkylation Approach Turočkin, Aleksej; Raven, William; Selig, Philipp European Journal of Organic Chemistry, Vol. 2017, Issue 2 https://doi.org/10.1002/ejoc.201601154	journal	December 2016
Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor Williams, Neil J.; Seipp, Charles A.; Garrabrant, Kathleen A. Chemical Communications, Vol. 54, Issue 72 https://doi.org/10.1039/c8cc05115a	journal	January 2018
Simple guanidinium motif for the selective binding and extraction of sulfate Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S. Separation Science and Technology, Vol. 53, Issue 12 https://doi.org/10.1080/01496395.2017.1318922	journal	March 2017
Simple guanidinium motif for the selective binding and extraction of sulfate Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S. Figshare, 35.58 kB https://doi.org/10.6084/m9.figshare.5162083	dataset	October 2017
Simple guanidinium motif for the selective binding and extraction of sulfate [Supplementary Data] Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S. Figshare-Supplementary information for journal article at DOI: 10.1080/01496395.2017.1318922, 1 docx (35.58 kB) https://doi.org/10.6084/m9.figshare.5162083.v2	preprint	October 2017

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CCDC 1404793: Experimental Crystal Structure Determination: PADFIM : bis(pyridin-2-ylamino)methaniminium chloride Space Group: P 21/n (14), Cell: a 14.0796(13)Å b 10.6907(10)Å c 16.9593(16)Å, α 90.00° β 109.751(2)° γ 90.00° Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S. https://doi.org/10.5517/cc1j4sxc The current record is supplemented by this dataset	dataset	June 2015
CCDC 1404794: Experimental Crystal Structure Determination: PADFOS : bis(pyridin-2-ylamino)methaniminium nitrate Seipp, Charles; Williams, Neil; Bryantsev, Vyacheslav https://doi.org/10.5517/cc1j4syd The current record is supplemented by this dataset	dataset	June 2015
CCDC 1404795: Experimental Crystal Structure Determination: PADFUY : bis(pyridin-2-ylamino)methaniminium hemisulfate methanol solvate dihydrate Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S. https://doi.org/10.5517/cc1j4szf The current record is supplemented by this dataset	dataset	June 2015
CCDC 1404796: Experimental Crystal Structure Determination: PADGAF : bis(pyridin-2-ylamino)methaniminium hemisulfate hydrate Seipp, Charles; Williams, Neil; Bryantsev, Vyacheslav https://doi.org/10.5517/cc1j4t0h The current record is supplemented by this dataset	dataset	June 2015