Abstract
We seek a theoretical method which is capable of predicting trends in the binding affinity of macrocyclic receptors for various anions in aqueous solution. Success has been achieved in this endeavor by employing semiempirical methodology to compute the energetics of certain exchange reactions whereby anions are exchanged between a macrocyclic receptor and a cluster of water molecules. The method is computationally tractable with workstation-class computing hardware and is applicable to a wide range of guest/host systems. Computations for several anion/receptor systems are reported.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R.M. Izatt, J.S. Bradshaw, S.A. Nielsen, J.D. Lamb, J.J. Christensen, and D. Sen:Chem. Rev. 85, 271 (1985).
J.S. Bradshaw, R.M. Izatt, R.L. Bruening, and J.J. Christensen:U.S. Patent 4,943,375 (Jul. 24, 1990).
R.M. Izatt, K. Pawlak, J.S. Bradshaw, and R.L. Bruening:Chem. Rev. 91, 1721 (1991).
C.J. Pedersen:J. Am. Chem. Soc. 89, 7017 (1967).
C.H. Park and H.E. Simmons:J. Am. Chem. Soc. 90, 2431 (1968).
X. Yang, C.B. Knobler, Z. Zheng, and M.F. Hawthorne:J. Am. Chem. Soc. 116, 7142 (1994).
D.E. Kaufmann and A. Otten:Angew. Chem. Int. Ed. Engl. 33, 1832 (1994).
T.P. Lybrand, J.A. McCammon, and G. Wipff:Proc. Natl. Acad. Sci. U.S.A. 83, 833 (1986).
B. Owenson, R.D. Macelroy, and A. Pohorille:J. Mol. Struct. THEOCHEM 179, 467 (1988).
B. Owenson, R.D. Macelroy, and A. Pohorille:J. Am. Chem. Soc. 110, 6992 (1988).
G. Wipff and J.-M. Wurtz:New J. Chem. 13, 807 (1989).
S. Jacobson and R. Pizer:J. Am. Chem. Soc. 115, 11216 (1993).
R.B. Shirts and L.D. Stolworthy:J. Incl. Phenom. 20, 297 (1995).
A.K. Rappe and W.A. Goddard:J. Phys. Chem. 95, 3358 (1991).
Z. Su:J. Comput. Chem. 14, 1036 (1993).
L. von Szentpály and I.L. Shamovsky:J. Molec. Struct. THEOCHEM 305, 249 (1994).
U. Sternberg, F.T. Koch, and M. Möllhoff:J. Comput. Chem. 15, 524 (1994).
D.B. Kireev, V.I. Fetisov, and N.S. Zefirov:J. Mol. Struct. THEOCHEM 304, 143 (1994).
G. Wipff, P. Weiner, and P. Kollman:J. Am. Chem. Soc. 104, 3249 (1982).
M.A. Thompson, E.D. Glendening, and D. Feller:J. Phys. Chem. 98, 10465 (1994).
B.P. Hay, J.R. Rustad, and C.J. Hostetler:J. Am. Chem. Soc. 115, 11158 (1993).
B.P. Hay and J.R. Rustad:J. Am. Chem. Soc. 116, 6316 (1994).
R.D. Hancock:Acc. Chem. Res. 23, 253 (1990).
E. Graf and J-M. Lehn:J. Am. Chem. Soc. 98, 6403 (1976).
A. Pullman, C. Giessner-Prettre, and Y.V. Kruglyak:Chem. Phys. Lett. 35, 156 (1975).
E.D. Glendening, D. Feller, and M.A. Thompson:J. Am. Chem. Soc. 116, 10657 (1994).
A.R. Katritzky, N. Malhotra, R. Ramanathan, R.C. Kemerait, Jr., J.A. Zirmnerman, and J.R. Eyler:Rapid Commun. Mass Spectrosc. 6, 25 (1992).
M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart:J. Am. Chem. Soc. 107, 3902 (1985).
T. Yamabe, K. Hori, K. Akagi, and K. Fukui:Tetrahedron 35, 1065 (1979)
K. Hori, H. Yamada, and T. Yamabe:Tetrahedron 39, 67 (1983).
I.N. Levine:Quantum Chemistry, Prentice Hall, Englewood Cliffs, NJ, Ch. 17 (1991).
ZINDO, J. Ridley and M. Zerner:Theoret. Chim. Acta 32, 111 (1973). J. Ridley and M. Zerner:Theoret. Chim. Acta 42, 223 (1976), as implemented in the CAChe Worksystem, CAChe Scientific, Inc. Beaverton, OR, U.S.A.
Z. Zheng, C.B. Knobler, C.E. Curtis, and M.F. Hawthorne:Inorg. Chem. 34, 432 (1995).
K. Worm, F.P. Schmidtchen, A. Schier, A. Schäfer, and M. Hesse:Angew. Chem. Int. Ed. Engl. 33, 327 (1994).
F.P. Schmidtchen:Angew. Chem. Int. Ed. Engl. 16, 720 (1977).
E. Graf and J-M. Lehn:J. Am. Chem. Soc. 97, 5022 (1975).
S.D. Reilly, G.R.K. Khalsa, D.K. Ford, J.R. Brainard, B.P. Hay, and P.H. Smith:Inorg. Chem. 34, 569 (1995).
E.D. Glendening and D. Feller:J. Phys. Chem. 99, 3060 (1995).
Editor V3.6, a part of the functionality of the CAChe Worksystem, CAChe Scientific, Inc. Beaverton, OR. U.S.A.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sohlberg, K., Tarbet, B.J. Computational prediction of trends in the selectivity of macrocyclic receptors for anions. J Incl Phenom Macrocycl Chem 23, 203–212 (1995). https://doi.org/10.1007/BF00709578
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00709578