The Journal of Organic Chemistry
Article
and ORTEP-3 for Windows.16 In all cases, non-hydrogen atoms were
treated anisotropically. Wherever possible, the hydrogen atoms were
located on a difference Fourier map and refined. In other cases, the
hydrogen atoms were geometrically fixed. Crystals of L and complex 2
included highly disordered and diffuse solvent molecules that could
not be properly modeled. The corresponding residual electron density
in these structures was treated with the SQUEEZE routine in
PLATON,17 which removed its contribution from the final hkl files.
Similarly, for complex 4 the highly disordered two TEA countercations
were treated as diffuse contributions to the overall scattering without
specific atom positions by SQUEEZE/PLATON.17 The presence of
(2) (a) Ravikumar, I.; Ghosh, P. Chem. Soc. Rev. 2012, 41, 3077−
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M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909−8913. (k) Brooks,
1
two TEA countercations was supported by the H NMR spectrum
recorded for crystals of complex 4.
1
NMR Studies. H NMR titration studies were done to determine
́
S. J.; Garcıa-Garrido, S. E.; Light, M. E.; Cole, P. A.; Gale, P. A. Chem.
the binding constants of L with different oxyanions in d6-DMSO at
room temperature. Initial concentrations were [ligand]0 = 5 mM and
[anion]0 = 50 mM. Each titration was performed by 10−15
measurements at room temperature. The association constant log K
was calculated by fitting urea NH signals using the EQNMR
program.11
Eur. J. 2007, 13, 3320−3329. (l) Brooks, S. J.; Gale, P. A.; Light, M. E.
Chem. Commun. 2006, 4344−4346. (m) Ravikumar, I.; Ghosh, P.
Chem. Commun. 2010, 46, 1082−1084. (n) Pramanik, A.; Khansari, M.
E.; Powell, D. R.; Fronczek, F. R.; Hossain, M. A. Org. Lett. 2014, 16,
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(3) (a) Rajbanshi, A.; Moyer, B. A.; Custelcean, R. Cryst. Growth Des.
2011, 11, 2702−2706. (b) Chutia, R.; Dey, S. K.; Das, G.
CrystEngComm 2013, 15, 9641−9647.
ASSOCIATED CONTENT
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S
* Supporting Information
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Commun. 2010, 46, 1394−1403. (b) Koblenz, T. S.; Wassenaar, J.;
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3438. (d) Rebek, J., Jr. Angew. Chem., Int. Ed. 2005, 44, 2068−2078.
Figures, a table, and CIF files giving characterization data for
the receptor L and its complexes 1−4, IR spectra, 13C NMR
1
1
and H NMR spectra, H NMR titration stack plots, fit plots,
LC-MS, crystallographic data, distance vs angle plots, and
hydrogen-bonding data. This material is available free of charge
(e) Lutzen, A. Angew. Chem., Int. Ed. 2005, 44, 1000−1002.
̈
́
(f) Gonzalez, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini,
A.; Pochini, A.; Prados, P.; Mendoza, J. de. Chem. Eur. J. 2000, 6, 73−
80. (g) Rudzevich, Y.; Rudzevich, V.; Schollmeyer, D.; Thondorf, I.;
AUTHOR INFORMATION
Corresponding Author
*G.D.: tel, +91-361-2582313; fax, +91-361-2582349; e-mail,
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Bohmer, V. Org. Lett. 2005, 7, 613−616. (h) Deng, C.; Fang, R.; Guan,
̈
Y.; Jiang, J.; Lin, C.; Wang, L. Chem. Commun. 2012, 48, 7973−7975.
(i) Singh, A. S.; Chen, B.-Y.; Wen, Y-S; Tsai, C.; Sun, S.-S. Org. Lett.
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Notes
(5) (a) Arunachalam, M.; Ghosh, P. Chem. Commun. 2011, 47,
8477−8492. (b) Custelcean, R. Chem. Commun. 2013, 49, 2173−2182.
(c) Gale, P. A. Acc. Chem. Res. 2006, 39, 465−475. (d) Busschaert, N.;
Wenzel, M.; Light, M. E.; Iglesias-Hernandez, P.; Perez-Tomas, R.;
Gale, P. A. J. Am. Chem. Soc. 2011, 133, 14136−14148. (e) Basu, A.;
Das, G. Dalton Trans. 2012, 41, 10792−10802. (f) Basu, A.; Das, G.
Chem. Commun. 2013, 49, 3997−3999. (g) Arunachalam, M.; Ghosh,
P. Chem. Commun. 2009, 5389−5391.
(6) (a) Seidel, S. R.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972−983.
(b) Yang, Z.; Wu, B.; Huang, X.; Liu, Y.; Li, S.; Xia, Y.; Jia, C.; Yanga,
X.-J. Chem. Commun. 2011, 47, 2880−2882. (c) Akhuli, B.; Ghosh, P.
Dalton Trans. 2013, 42, 5818−5825. (d) Turner, D.; Hursthouse, R.
M. B.; Light, M. E.; Steed, J. W. Chem. Commun. 2004, 1354−1355.
(e) Custelcean, R.; Bonnesen, P. V.; Roach, B. D.; Duncan, N. C.
Chem. Commun. 2012, 48, 7438−7440. (f) Li, S.; Jia, C.; Wu, B.; Luo,
Q.; Huang, X.; Yang, Z.; Li, Q.-S.; Yang, X.-J. Angew. Chem., Int. Ed.
2011, 50, 5721−5724. (g) Custelcean, R.; Bonnesen, P. V.; Duncan,
N. C.; Zhang, X.; Watson, L. A.; Berkel, G. V.; Parson, W. B.; Hay, B.
P. J. Am. Chem. Soc. 2012, 134, 8525−8534.
(7) Dey, S. K.; Das, G. Cryst. Growth Des. 2009, 10, 750−760.
(8) Dutta, B. K.; Kar, C.; Basu, A.; Das, G. Tetrahedron Lett. 2013, 54,
771−774.
(9) Hay, B. P.; Firman, T. K.; Moyer, B. A. J. Am. Chem. Soc. 2005,
127, 1810−1819.
(10) (a) Wang, T.; Yan, X.-P. Chem. Eur. J. 2010, 16, 4639−4649.
(b) Maeda, H.; Kusunose, Y. Chem. Eur. J. 2005, 11, 5661−5666.
(c) Brooks, S. J.; Gale, P. A.; Light, M. E. CrystEngComm 2005, 7,
586−591. (d) Juwarker, H.; Jeong, K.-S. Chem. Soc. Rev. 2010, 39,
3664−3674. (e) Basu, A.; Das, G. Inorg. Chem. 2012, 51, 882−889.
(11) Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311−312.
(12) Sheldrick, G. M. SAINT and XPREP, 5.1 ed.; Siemens Industrial
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The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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G.D. gratefully acknowledges the Council of Scientific and
Industrial Research (01/2727/13/EMR-II) and Science &
Engineering Research Board (SR/S1/OC-62/2011), New
Delhi, India, for financial support. We thank the CIF,
Department of Chemistry IIT Guwahati, and DST-FIST for
research support. A.B. thanks IIT Guwahati for a fellowship.
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