Journal of the American Chemical Society
Page 4 of 5
(11)
(12)
Li, W. -L.; Yong Li, Y.; Xu, C. -Q.; Wang, X-B.; Vorpagel, E.;
Li, J. Inorg. Chem. 2015, 54, 11157.
(a)
1
2
3
4
5
6
7
8
Theilacker, K.; Schlegel, H. B.; Kaupp, M.; Schwerdtfeger, P.
Inorg. Chem. 2015, 54, 9869.
Tiekink, E. R. T. Coord. Chem. Rev. 2017, 345, 209.
Yi, H-B.; Lee, H. M.; Kim, K. S. J. Chem. Theory Comput. 2009,
5, 1709.
It is worth noting that the two receptors in this study do not bind
purely ionic salts such as NaCl or CaCl2.
Gold Ore Processing Project Development and Operations;
Adams, M. D., Ed.; 2nd Ed.; Elsevier, 2016.
Liu, Z.; Frasconi, M.; Lei, J.; Brown, Z. J.; Zhu, Z.; Cao, D.; Iehl,
J.; Liu, G.; Fahrenbach, A. C.; Botros, Y. Y.; Farha, O. K.; Hupp,
J. T.; Mirkin, C. A.; Stoddart, J. F. Nat. Commun. 2013, 4, 1855.
Liu, Z.; Samanta, A.; Lei, J.; Sun, J.; Wang, Y.; Stoddart, J. F. J.
Am. Chem. Soc. 2016, 138, 11643.
Peck, E. M.; Liu, W.; Spence, G. T.; Shaw, S. K.; Davis, A. P.;
Destecroix, H.; Smith, B. D. J. Am. Chem. Soc. 2015, 137, 8668.
Liu, W.; Gómez-Durán, C. F. A.; Smith, B. D. J. Am. Chem. Soc.
2017, 139, 6390.
Gassensmith, J. J.; Arunkumar, E.; Barr, L.; Baumes, J. M.;
DiVittorio, K. M.; Johnson, J. R.; Noll, B. C.; Smith, B. D. J. Am.
Chem. Soc. 2007, 129, 15054.
Ke, C.; Destecroix, H.; Crump, M. P.; Davis, A. P. Nat. Chem.
2012, 4, 718.
Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580.
Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García,
J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498.
Tiekink, E. R. T.; Zukerman-Schpector, J. CrystEngComm 2009,
11, 1176.
Caracelli, I.; Zukerman-Schpector, J.; Tiekink, E. R. T. Gold Bull.
2013, 46, 81.
Brooner, R. E. M.; Widenhoefer, R. A. Angew. Chem. Int. Ed.
2013, 52, 11714.
There was no discernible correlation of calculated quadrupole
moment or polarizability for M1 and M2 (see Tables S8 and S9)
with receptor affinities for the gold complexes.
Chênevert, R.; Chamberland, D.; Simard, M.; Brisse, F. Can. J.
Chem. 1989, 67, 32.
Fábry, J.; Dušek, M.; Fejfarová, K.; Krupková, R.; Vaněk, P.;
Němec, I. Acta Crystallogr. C. 2004, C60, m426.
Lassahn, P.; Lozan, V.; Janiak, C. Dalton Trans. 2003, 927.
Mahadevi, A. S.; Sastry, G. N. Chem. Rev. 2016, 116, 2775.
Dong, C. C.; Xiang, J. F.; Xu, L. J.; Gong, H. Y. Tetrahedron
Lett. 2018, 59, 264.
(13)
(14)
(15)
(16)
(17)
9
(b)
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(18)
(19)
(20)
(21)
(22)
(23)
(24)
(25)
(26)
(27)
(28)
Figure 5. Different views of the X-ray crystal structure for
(a) M2•PtCl4 , and (b) M2•Pd2Cl6 . Tetrabutylammonium
counter cations omitted for clarity.
-2
-2
ASSOCIATED CONTENT
Supporting Information.
Chemical synthesis and characterization, NMR titrations,
mass spectral data, X ray crystal data, RDG analyses, DFT
calculations. The Supporting Information (PDF) is available
free of charge on the ACS Publications website.
(29)
(30)
(31)
(32)
(33)
AUTHOR INFORMATION
Corresponding Author
(34)
Preliminary binding studies using a water soluble version of M1
(see reference 19 for the structure) or M2 have measured Ka ~104
*smith.115@nd.edu
Notes
The authors declare no competing financial interest.
M-1 for binding AuCl4- or AuBr4 in water or 100 mM phosphate
-
buffer. AuCl4- and AuBr4- are known to be relatively hydrophobic
anions and ongoing studies aim to determine if the hydrophobic
effect is the dominant factor driving guest encapsulation.
Syed, S. Hydrometallurgy 2012, 115–116, 30.
Do, J. L.; Tan, D.; Friščić, T. Angew. Chem. Int. Ed. 2018, 57,
2667.
ACKNOWLEDGMENT
(35)
(36)
We are grateful for funding support from the NSF
(CHE1708240). We thank S. Brown and A. G. Lappin for
helpful comments.
(37)
(38)
(39)
Akcil, A.; Erust, C.; Gahan, C. S.; Ozgun, M.; Sahin, M.; Tuncuk,
A. Waste Manag. 2015, 45, 258.
Nam, S. H.; Lee, W. M.; Shin, Y. J.; Yoon, S. J.; Kim, S. W.;
Kwak, J. Il; An, Y. J. Water Res. 2014, 48, 126.
Zodrow, K. R.; Li, Q.; Buono, R. M.; Chen, W.; Daigger, G.;
Duenas-Osorio, L.; Elimelech, M.; Huang, X.; Jiang, G.; Kim, J.-
H.; Logan, B. E.; Sedlak, D. L.; Westerhoff, P.; Alvarez, P. J. J.
Environ. Sci. Technol. 2017, 51, 10274.
Zhitenko, L. P. Inorg. Mater. 2013, 49, 1294.
Raubenheimer, H. G.; Schmidbaur, H. J. Chem. Educ. 2014, 91,
2014.
Jones, A. C. Top. Curr. Chem. 2015, 357, 133.
Belo, D.; Almeida, M. Coord. Chem. Rev. 2010, 254, 1479.
Serpell, C. J.; Cookson, J.; Ozkaya, D.; Beer, P. D. Nat. Chem.
2011, 3, 478.
Gabbiani, C.; Casini, A.; Messori, L. Gold Bull. 2007, 40, 73.
Lazarević, T.; Rilak, A.; Bugarčić, Ž. D. Eur. J. Med. Chem.
2017, 142, 8.
REFERENCES
(1)
(2)
(3)
Mercer, D. J.; Loeb, S. J. Chem. Soc. Rev. 2010, 39, 3612.
Liu, Z.; Schneebeli, S. T.; Stoddart, J. F. Chimia. 2014, 68, 315.
Zhao, M.; Wang, H.-B.; Ji, L.-N.; Mao, Z.-W. Chem. Soc. Rev.
2013, 42, 8360.
Steed, J. W. Coord. Chem. Rev. 2001, 215, 171.
Colquhoun, H. M.; Doughty, S. M.; Slawin, A. M. Z.; Stoddart,
J. F.; Williams, D. J. Angew. Chem. Int. Ed. 1985, 24, 135.
Ferguson, G.; Matthes, K. E.; Parker, D. Angew. Chem. Int. Ed.
1987, 26, 1162.
Kickham, J. E.; Loeb, S. J.; Murphy, S. L. J. Am. Chem. Soc.
1993, 115, 7031.
Kickham, J. E.; Loeb, S. J. Chem. Commun. 1993, 25, 1848.
Blight, B. A.; Wisner, J. A.; Jennings, M. C. Chem. Commun.
2006, 4593.
(40)
(41)
(4)
(5)
(42)
(43)
(44)
(6)
(7)
(45)
(46)
(8)
(9)
(10)
Zigon, N.; Kyritsakas, N.; Hosseini, M. W. Dalton Trans. 2014,
43, 152.
ACS Paragon Plus Environment