The Structure of m-Xylylenediguanidinium Sulfate: A Putative Molecular Tweezer Ligand for Anion Chelation
While solution 1H and 13C NMR spectra of the sulfate salt of m-xylylenediguanidinium dication 2 indicate a symmetrical conformation for the cation, a single-crystal X-ray structural determination of 2 reveals that this dication does not offer symmetrical tweezer-like coordination toward sulfate in t...
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| Published in: | Crystal growth & design Vol. 1; no. 4; pp. 339 - 342 |
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American Chemical Society
01-07-2001
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| Abstract | While solution 1H and 13C NMR spectra of the sulfate salt of m-xylylenediguanidinium dication 2 indicate a symmetrical conformation for the cation, a single-crystal X-ray structural determination of 2 reveals that this dication does not offer symmetrical tweezer-like coordination toward sulfate in the solid state (consistent with solid phase 13C NMR spectra) but rather assembles into a complex three-dimensional H-bonded network in which the two guanidinium arms adopt different conformations, and all guanidinium N−H units plus one C−H unit of each CH2 group are involved in H-bonds to sulfate. |
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| AbstractList | While solution 1H and 13C NMR spectra of the sulfate salt of m-xylylenediguanidinium dication 2 indicate a symmetrical conformation for the cation, a single-crystal X-ray structural determination of 2 reveals that this dication does not offer symmetrical tweezer-like coordination toward sulfate in the solid state (consistent with solid phase 13C NMR spectra) but rather assembles into a complex three-dimensional H-bonded network in which the two guanidinium arms adopt different conformations, and all guanidinium N−H units plus one C−H unit of each CH2 group are involved in H-bonds to sulfate. |
| Author | McGeorge, Gary Hutchings, Michael G Grossel, Martin C Kenworthy, Mark Chippendale, A. Margaret Merckel, Daniel A. S |
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| CitedBy_id | crossref_primary_10_1002_anie_200352731 crossref_primary_10_1021_jp052799c crossref_primary_10_3184_174751912X13271656638889 crossref_primary_10_3184_030823410X12792161080778 crossref_primary_10_1080_10610278_2017_1394462 crossref_primary_10_1002_ange_200352731 crossref_primary_10_1016_j_polymer_2014_07_037 crossref_primary_10_3184_030823410X12664920874109 crossref_primary_10_1016_j_bpc_2009_06_002 |
| Cites_doi | 10.1002/anie.199621261 10.1016/S0040-4039(97)00513-3 10.1021/ja00075a021 10.1002/jlac.199419940110 10.1107/S0021889899006020 10.1021/ja00084a039 10.1021/jo982418+ 10.1002/anie.199708621 10.1021/cr9603845 10.1021/cm9600743 10.1002/anie.199512371 10.1021/ja00484a010 10.1002/hlca.19960790719 |
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| Title | The Structure of m-Xylylenediguanidinium Sulfate: A Putative Molecular Tweezer Ligand for Anion Chelation |
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