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. 2011 Jun 21;9(12):4444-7.
doi: 10.1039/c1ob05052d. Epub 2011 Mar 21.

Seven-coordinate anion complex with a tren-based urea: binding discrepancy of hydrogen sulfate in solid and solution states

Avijit Pramanik  1 , Bethtrice Thompson, Trina Hayes, Kimberly Tucker, Douglas R Powell, Peter V Bonnesen, Erick D Ellis, Ken S Lee, Hongtao Yu, Md Alamgir Hossain
Affiliations

Seven-coordinate anion complex with a tren-based urea: binding discrepancy of hydrogen sulfate in solid and solution states

Avijit Pramanik et al. Org Biomol Chem. .

Abstract

Structural characterization of a hydrogen sulfate complex with a tren-based urea suggests that the anion is coordinated with six NH···O bonds (d(N···O) = 2.857 (3) to 3.092 (3) Å) and one OH···O bond (d(O···O) = 2.57 (2) Å) from three receptors; however, in solution the anion is bound within the pseudo-cavity of one receptor.

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Figures

Fig. 1
Fig. 1
Tren-based urea (L) and its X-ray structure (1).
Fig. 2
Fig. 2
X-ray structure of the hydrogen sulfate complex with L showing seven hydrogen bonds (six NH ··· O and one OH ··· O bonds).
Fig. 3
Fig. 3
The coordination environment of bisulfate showing seven hydrogen bonds from three ureas.
Fig. 4
Fig. 4
1H NMR titration curves of L (2 mM) with n-Bu4 NHSO4 (●, ▲) and ZnSO4 (○, △) in DMSO-d6. Net changes in the chemical shifts of NH are shown against the increasing amount of anion (20 mM). H1 = CH2 NHCO and H2 = CONHAr.
Fig. 5
Fig. 5
2D NOESY NMR experiments of L in absence (A) and presence (B) of hydrogen sulfate (5 equiv.) in DMSO-d6.
Fig. 6
Fig. 6
Proposed binding mode of L for hydrogen sulfate in solution.
See this image and copyright information in PMC

References

    1. Antonisse MMG, Reinhoudt DN. Chem Commun. 1998:443–448.
    2. Atwood JL, Holman KT, Steed JW. Chem Commun. 1996:1401–1407.
    3. Gale PA. Coord Chem Rev. 2003;240:191–221.
    4. Cormode DP, Murray SS, Cowley AR, Beer PD. Dalton Trans. 2006:5135–5140. - PubMed
    1. Pflugrath JW, Quiocho FA. Nature. 1985;314:257–260. - PubMed
    1. Moyer BA, Delmau LH, Fowler CJ, Ruas A, Bostick DA, Sessler JL, Katayev E, Pantos GD, Llinares JM, Hossain MA, Kang SO, Bowman-James K. Adv Inorg Chem. 2007;59:175–204.
    1. Kang SO, Hossain MA, Powell D, Bowman-James K. Chem Commun. 2005:328–330. - PubMed
    2. Mani G, Guchhait T, Kumar R, Kumar S. Org Lett. 2010;12:3910–3913. - PubMed
    3. Mendy JS, Pilate M, Horne T, Day VW, Hossain MA. Chem Commun. 2010;46:6084–6086. - PMC - PubMed
    4. Saeed MA, Fronczek FR, Powell DR, Hossain MA. Tetrahedron Lett. 2010;51:4233–4236. - PMC - PubMed
    1. Hossain MA, Llinares JM, Powell D, Bowman-James K. Inorg Chem. 2001;40:2936–2937. - PubMed
    2. Kang SO, Day VW, Bowman-James K. Org Lett. 2009;11:3654–3657. - PubMed
    3. Lakshminarayanan PS, Suresh E, Ghosh P. Inorg Chem. 2006;45:4373–4380. - PubMed

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