Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Aug 21;49(65):7240-2.
doi: 10.1039/c3cc44574g. Epub 2013 Jul 10.

Aryl C-H···Cl(-) hydrogen bonding in a fluorescent anion sensor

Blakely W Tresca  1 , Lev N Zakharov, Calden N Carroll, Darren W Johnson, Michael M Haley
Affiliations

Aryl C-H···Cl(-) hydrogen bonding in a fluorescent anion sensor

Blakely W Tresca et al. Chem Commun (Camb). .

Abstract

A new phenyl-acetylene receptor containing a carbonaceous hydrogen bond donor activates anion binding in conjunction with two stabilizing ureas. The unusual CH···Cl(-) hydrogen bond is apparent in solution by large (1)H NMR chemical shifts and by a short, linear contact in the solid state.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Structures of 2,6-bis(2-anilinoethynyl)arene cores 1 and 4 and anion receptors 2, 3 and 5.
Fig. 2
Fig. 2
1H NMR titration of 5 with TBA+Cl– at 298 K; [5] = 0.69 mM in water saturated CDCl3. Peak assignments refer to Scheme 1.
Fig. 3
Fig. 3
X-ray crystal structure of 5•Cl– shown as ORTEP representation. Hydrogen bond interactions are shown as dashed lines. Non-coordinating hydrogens, TBA+ counter cation and solvent have been omitted for clarity. Ellipsoids drawn at 50% probability level.
Scheme 1
Scheme 1
Synthesis of receptor 5. Proton assignments determined via 1H-13C HSQC and 1H-1H ROSY NMR spectroscopy.
See this image and copyright information in PMC

References

    1. Sessler JL, Gale PA, Cho W-S. Anion Receptor Chemistry. Royal Society of Chemistry; Cambridge: 2006.
    1. Beer PD, Gale PA. Angew. Chem. Int. Ed. 2001;40:486–516. - PubMed

    1. Bordwell FG. Acc. Chem. Res. 1988;21:456–463. There appears to be discrepancy for the pKa of benzene in water, with values of 37 and 43 appearing most commonly. We chose to use the value reported in: Anslyn EV, Dougherty DA. Modern Physical Organic Chemistry. University Science Books; Sausalito, CA: 2006. p. 280.

    1. Desiraju GR, Steiner T. The Weak Hydrogen Bond: in Structural Chemistry and Biology. Oxford University Press; Oxford; New York: 1999.
    1. Schneider H-J. Angew. Chem. Int. Ed. 2009;48:3924–3977. - PubMed

Publication types