17 P. R. Ashton, B. Ho¨rner, O. Kocian, S. Menzer, A. J. P. White, J. F.
Stoddart and D. J. Williams, Synthesis, 1996, 8, 930–940.
18 V. Bo¨hmer, D. Meshcheryakov, I. Thondorf and M. Bolte, Acta
Crystallogr., Sect. C, 2004, 60, o136–o139.
19 D. Meshcheriakov, V. Bo¨hmer, and M. Bolte, unpublished results.
20 Bonds shown by dashed lines were defined by Mercury v. 1.41 –
Mercury: visualization and analysis of crystal structures: C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Crystallgr., 2006, 39, 453–
457.
21 M. C. Etter, Z. Urbanczyk-Lipkowska, M. Zia-Ebrahimi and T. W.
Panunto, J. Am. Chem. Soc., 1990, 112, 8415–8426.
22 It should be noted that by choosing different starting structures further
conformations stable on the MD timescale were obtained. Since these
conformations are higher in energy we restrict the discussion to the
most stable conformations.
References and notes
1 For a general review on anion receptor chemistry see: J. L. Sessler,
P. A. Gale and W. Cho, in Anion Receptor Chemistry, Monographs
in Supramolecular Chemistry, ed. J. F. Stoddart, Royal Society of
Chemistry, 2006; P. A. Gale and R. Quesada, Coord. Chem. Rev., 2006,
250, 3219–3244; P. A. Gale, Sergio E. Garc´ıa-Garrido and J. Garric,
Chem. Soc. Rev., 2008, 37, 151–190; P. D. Beer and P. A. Gale, Angew.
Chem., Int. Ed., 2001, 40, 486–516.
2 A. P. Bisson, V. M. Lynch, M. C. Monahan and E. V. Anslyn, Angew.
Chem., Int. Ed., 1997, 36, 2340–2342.
3 For general review on nitrate receptors see: O. A. Okunola, P. V.
Santacroce and J. T. Davis, Supramol. Chem., 2008, 20, 169–190; P.
Blondeau, J. Benet-Buchholz and J. de Mendoza, New J. Chem., 2007,
31, 736–740.
4 R. Herges, A. Dikmans, U. Jana, F. Ko¨hler, P. G. Jones, I. Dix, T. Fricke
and B. Ko¨nig, Eur. J. Org. Chem., 2002, 3004–3014.
5 For a recent review seeJ. L. Sessler, S. Camiolo and P. A. Gale, Coord.
Chem. Rev., 2003, 240, 17–55.
23 For the simulation of the complexes in chloroform see the ESI.
24 H. Gampp, M. Maeder, C. J. Meyer and A. D. Zuberbu¨hler, Talanta,
1985, 32, 257–264.
6 C. R. Bondy and S. J. Loeb, Coord. Chem. Rev., 2003, 240, 77–99; M. J.
Chmielewski and J. Jurczak, Chem. Eur. J., 2005, 11, 6080–6094.
7 S. J. Brooks, S. E. Garc´ıa-Garrido, M. E. Light, P. A. Cole and P. A.
Gale, Chem. Eur. J., 2007, 13, 3320–3329; B. H. M. Snellink-Rue¨l,
M. M. G. Antonisse, J. F. J. Engbersen, P. Timmermann and D. N.
Reinhoudt, Eur. J. Org. Chem., 2000, 165–170; D. Ranganathan and C.
Lakshmi, Chem. Commun., 2001, 1250–1251.
8 Y. Morzherin, D. M. Rudkevich, W. Verboom and D. N. Reinhoudt,
J. Org. Chem., 1993, 58, 7602–7605; A. Casnati, L. Pirondini, N. Pelizzi
and R. Ungaro, Supramol. Chem., 2000, 12, 53–65; M. D. Lankshear,
A. R. Cowley and P. D. Beer, Chem. Commun., 2006, 612–614; B.
Schazmann, N. Alhashimy and D. Diamond, J. Am. Chem. Soc., 2006,
128, 8607–8614.
9 K. Choi and A. D. Hamilton, J. Am. Chem. Soc., 2003, 125, 10241–
10249; S. Kubik, R. Goddard, R. Kirchner, D. Nolting and J. Seidel,
Angew. Chem., Int. Ed., 2001, 40, 2648–2651.
10 M. A. Hossain, S. O. Kang, D. Powell and K. Bowman-James, Inorg.
Chem., 2003, 42, 1397–1399.
11 K. D. Shimizu and J. Rebek, Jr., Proc. Natl. Acad. Sci. U. S. A., 1995, 92,
12403–12407; Shivanyuk, M. Saadioui, F. Broda, I. Thondorf, M. O.
Vysotsky, K. Rissanen, E. Kolehmainen and V. Bo¨hmer, Chem. Eur. J.,
2004, 10, 2138–2148; Y. Rudzevich, V. Rudzevich, D. Schollmeyer, I.
Thondorf and V. Bo¨hmer, Org. Lett., 2005, 7, 613–616.
12 B. P. Hay, M. Gutowski, D. A. Dixon, J. Garza, R. Vargas and B. A.
Moyer, J. Am. Chem. Soc., 2004, 126, 7925–7934; B. P. Hay, T. K.
Firman and B. A. Moyer, J. Am. Chem. Soc., 2005, 127, 1810–1819.
13 D. Meshcheryakov, F. Arnaud-Neu, V. Bo¨hmer, M. Bolte, V. Hubscher-
Bruder, E. Jobin, I. Thondorf and Sabine Werner, Org. Biomol. Chem.,
2008, 6, 1004–1014.
25 D. A. Case, D. A. Pearlman, J. W. Caldwell, T. E. Cheatham III, J.
Wang, W. S. Ross, C. L. Simmerling, T. A. Darden, K. M. Merz, R. V.
Stanton, A. L. Cheng, J. J. Vincent, M. Crowley, V. Tsui, H. Gohlke,
R. J. Radmer, Y. Duan, J. Pitera, I. Massova, G. L. Seibel, U. C. Singh,
P. K. Weiner, and P. A. Kollman, AMBER 7, University of California,
San Francisco, USA, 2002; D. A. Pearlman, D. A. Case, J. W. Caldwell,
W. S. Ross, T. E. Cheatham III, S. DeBolt, D. Ferguson, G. Seibel and
P. A. Kollman, Comput. Phys. Commun., 1995, 91, 1–41.
26 C. I. Bayly, P. Cieplak, W. D. Cornell and P. A. Kollman, J. Phys. Chem.,
1993, 97, 10269–10280.
27 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E.
Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels,
K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M.
Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford,
J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma,
P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K.
Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul,
B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.
Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham,
C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G.
Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-
Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision
A.11), Gaussian, Inc., Pittsburgh, PA, 2001.
28 T. Fox and P. Kollman, J. Phys. Chem. B, 1998, 102, 8070–8079; P.
Cieplak, J. Caldwell and P. Kollman, J. Comput. Chem., 2001, 22, 1048–
1057.
29 X. Grabuleda, C. Jaime and P. A. Kollman, J. Comput. Chem., 2000,
21, 901–908.
14 D. Meshcheryakov, V. Bo¨hmer, M. Bolte, V. Hubscher-Bruder, F.
Arnaud-Neu, H. Herschbach, A. Van Dorsselaer, I. Thondorf and
W. M o¨gelin, Angew. Chem., Int. Ed., 2006, 45, 1648–1652.
15 B. B. C. Hamann, N. R. Branda and J. Rebek, Jr., Tetrahedron Lett.,
1993, 34, 6837–6840.
16 P. Bu¨hlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron,
1997, 53, 1647–1654; V. Alca´zar, M. Segura, P. Prados and J. de
Mendoza, Tetrahedron Lett., 1997, 39, 1033–1036.
30 P. D. Kirchhoff, M. B. Bass, B. A. Hanks, J. M. Briggs, A. Collet and
J. A. McCammon, J. Am. Chem. Soc., 1996, 118, 3237–3246.
31 T. Darden, D. York and L. Pedersen, J. Chem. Phys., 1993, 98, 10089–
10092; U. Essmann, L. Perera, M. L. Berkowitz, T. Darden, H. Lee and
L. G. Pederson, J. Chem. Phys, 1995, 103, 8577–8593.
32 SYBYL 7.2, Tripos, Inc., St. Louis, USA.
33 X-AREA, 2001, Stoe & Cie, Darmstadt, Germany.
34 G. M. Sheldrick, Acta Crystallgr., Sect. A, 2008, 64, 112–122.
This journal is
The Royal Society of Chemistry 2008
Org. Biomol. Chem., 2008, 6, 3244–3255 | 3255
©