Host-Guest Complexes of Two Isomeric 2,2’-Bioxazole Based {2}-Lehn-Type Cryptands. Prediction of Ion Selectivity by Quantum Chemical Calculations. Part XIV

Dušan Ćoćić,^a,b,c,d Selina Siegl,^e Aliya Manaa,^e Svetlana Begel,^a Colin D. Hubbard,^f and Ralph Puchta^a,b,c,e@

Dedicated to the 75^th birthday of our friend and teacher Prof. Dr. Dr. h.c. mult. Rudi van Eldik

^aInorganic Chemistry, Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, 91058 Erlangen, Germany

^bCentral Institute for Scientific Computing (ZISC), University of Erlangen-Nuremberg, 91058 Erlangen, Germany

^cComputer Chemistry Center, Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, 91052 Erlangen, Germany

^dDepartment of Chemistry, Faculty of Science, University of Kragujevac, 34000 Kragujevac, Serbia

^eLothar-von-Faber-Schule, Staatliche Fachoberschule Nürnberg, 90411 Nuremberg, Germany

^fDepartment of Chemistry, University of New Hampshire, 03824 New Hampshire, USA

^@Corresponding author E-mail: Ralph.Puchta@fau.de

DOI: 10.6060/mhc200603p
Macroheterocycles 2020 13(3) 215-222

The two isomeric cryptands 1 (N,N’-bis(2,2’-bioxazole-5,5’-dimethyl)-2,2’-bioxazole-5,5’-bis(methylamine)) and 2 (N,N’-bis(2,2’-bioxazole-4,4’-dimethyl)-2,2’-bioxazole-4,4’-bis(methylamine)) were investigated by DFT-calculations (RB3LYP/LANL2DZp). Based on these structures and energies we have determined with model equations and by structural comparison with solvent complexes ([M(Furan)_n]^m+, [M(Pyridine)_n]^m+ and [M(NH₃)_n]^m+) the ion selectivity of 1 and 2. 1 exhibits preferences for the sodium cation and the calcium dication, nearly equally with the strontium dication. Therefore, 1 has a cavity comparable to [phen.phen.phen]. In contrast, cryptand 2, although it also shows a preference for the third-row sodium cation, for the third-row alkaline earth cation Mg²⁺. Therefore, the cavity size must be similar to that of Bühl’s cryptand dodeka(ethylene)octamine and [2.1.1]. We attribute this difference in selectivity to the longer M^m+-N-interactions in 2 compared to M^m+-O-interactions in 1.

References:

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1. Pedersen C.J. J. Am. Chem. Soc. 1967, 89, 2495-2496.
https://doi.org/10.1021/ja00986a052

2. a) Dietrich B., Lehn J.-M., Sauvage J.-P. Tetrahedron Lett. 1969, 10, 2889-2892;
https://doi.org/10.1016/S0040-4039(01)88300-3
b) Dietrich B., Lehn J.-M., Sauvage J.-P. Tetrahedron Lett. 1969, 10, 2885-2888.
https://doi.org/10.1016/S0040-4039(01)88299-X

3. a) Pedersen C.J. Angew. Chem. 1988, 100, 1053-1059;
https://doi.org/10.1002/ange.19881000805
b) Pedersen C.J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1021-1027;
https://doi.org/10.1002/anie.198810211
c) Cram D.J. Angew. Chem. 1988, 100, 1041-1052;
https://doi.org/10.1002/ange.19881000804
d) Cram D.J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
https://doi.org/10.1002/anie.198810093
e) Lehn J.-M. Angew. Chem. 1988, 100, 91-116;
https://doi.org/10.1002/ange.19881000110
f) Lehn J.-M. Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112.
https://doi.org/10.1002/anie.198800891

4. a) Müller W.H. Naturwissenschaften 1970, 57, 248.
https://doi.org/10.1007/BF01010278
b) Lehn J.-M., Montavon F. Helv. Chim. Acta 1978, 61, 67-76;
https://doi.org/10.1002/hlca.19780610107
c) Lehn J.-M., Kirch M. Angew. Chem. 1975, 87, 542-543.
https://doi.org/10.1002/ange.19750871507

5. a) Ajgaonkar H.S., Khopkar S.M. Chem. Anal. 1999, 44, 61-66;
b) Tait D., Haase G., Wiechen A. Kieler Milchwirtschaftl. Forschungsber. 1998, 50, 211-217.

6. Burai L., Scopelliti R., Tóth E. Chem. Commun. 2002, 43, 2366-2367.
https://doi.org/10.1039/B206709A

7. Li H., Shih J.S. J. Chin. Chem. Soc. 1999, 46, 885-892.
https://doi.org/10.1002/jccs.199900120

8. Housecroft C.E. Clusterverbindungen von Hauptgruppenelementen. Weinheim: VCH, 1994.

9. Farahbakhsh M., Schmidt H., Rehder D. Chem. Ber. Recl. 1997, 130, 1123-1127.
https://doi.org/10.1002/cber.19971300814

10. a) Dye J.L., Wagner M.J., Overney G., Huang R.H., Nagy T.F., Tománek D. J. Am. Chem. Soc. 1996, 118, 7329-7336.
https://doi.org/10.1021/ja960548z
b) Dale S.G., Otero-de-la-Roza A., Johnson E.R. Phys. Chem. Chem. Phys. 2014, 16, 14584-14593.
https://doi.org/10.1039/C3CP55533J

11. Puchta R., Meier R., van Eldik R. Aust. J. Chem. 2007, 60, 889-897.
https://doi.org/10.1071/CH07238

12. Begel S., Scheurer A., Puchta R., van Eldik R. Z. Anorg. Allg. Chem. 2016, 642, 395-402.
https://doi.org/10.1002/zaac.201600019

13. Puchta R., van Eldik R. Eur. J. Inorg. Chem. 2007, 1120-1127.
https://doi.org/10.1002/ejic.200600715

14. a) Becke A.D. J. Phys. Chem. 1993, 97, 5648-5652;
https://doi.org/10.1063/1.464913
b) Lee C., Yang W., Parr R.G. Phys. Rev. B 1988, 37, 785-789;
https://doi.org/10.1103/PhysRevB.37.785
c) Stephens P.J., Devlin F.J., Chabalowski C.F., Frisch M.J. J. Phys. Chem. 1994, 98, 11623-11627.
https://doi.org/10.1021/j100096a001

15. a) Dunning Jr.T.H., Hay P.J. Mod. Theor. Chem. 1976, 3, 1-28;
https://doi.org/10.1063/1.88610
b) Hay P.J., Wadt W.R. J. Chem. Phys. 1985, 82, 270-283;
https://doi.org/10.1063/1.448799
c) Hay P.J., Wadt W.R. J. Chem. Phys. 1985, 82, 284-298;
https://doi.org/10.1063/1.448800
d) Hay P.J., Wadt W.R. J. Chem. Phys. 1985, 82, 299-310.
https://doi.org/10.1063/1.448975

16. Gaussian Basis Sets for Molecular Calculations (Huzinaga S., Ed.) Amsterdam: Elsevier, 1984.

17. a) Shyshov O., Brachvogel R.-Ch., Bachmann T., Srikantharajah R., Segets D., Hampel F., Puchta R., von Delius M. Angew. Chem. 2017, 129, 794-799; Angew. Chem. Int. Ed. 2017, 56, 776-781;
https://doi.org/10.1002/ange.201609855
b) Puchta R., Meier R., van Eikema Hommes N.J.R., van Eldik R. Eur. J. Inorg. Chem. 2006, 4063-4067;
https://doi.org/10.1002/ejic.200600483
c) Scheurer A., Maid H., Hampel F., Saalfrank R.W., Toupet L., Mosset P., Puchta R., van Eikema Hommes N.J.R. Eur. J. Org. Chem. 2005, 2566-2574;
https://doi.org/10.1002/ejoc.200500042
d) Illner P., Zahl A., Puchta R., van Eikema Hommes N.J.R., Wasserscheid P., van Eldik R. J. Organomet. Chem. 2005, 690, 3567-3576;
https://doi.org/10.1016/j.jorganchem.2005.03.029
e) Weber C.F., Puchta R., van Eikema Hommes N.J.R., Wasserscheid P., van Eldik R. Angew. Chem. 2005, 117, 6187-6192; Angew. Chem. Int. Ed. 2005, 44, 6033-6038.
https://doi.org/10.1002/ange.200501329

18. Gaussian 09, Revision C.01. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakat-suji H., Caricato M., Li H., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Jr., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jara-millo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Moro-kuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannen-berg J.J., Dapprich S., Daniels A.D., Farkas O., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D.J. Gaussian, Inc., Wallingford CT, 2010.

19. Puchta R., Begel S., van Eldik R. Adv. Inorg. Chem. 2019, 73, 445-505.
https://doi.org/10.1016/bs.adioch.2018.10.005

20. Puchta R., Ćoćić D., Michel M., van Eldik R. J. Coord. Chem. 2019, 72, 2106-2114.
https://doi.org/10.1080/00958972.2019.1636975

21. Puchta R., Pasgreta E., van Eldik R. Adv. Inorg. Chem. 2009, 61, 523-571.
https://doi.org/10.1016/S0898-8838(09)00209-8

22. Hollemann A.F., Wiberg N. Lehrbuch der Anorganischen Chemie. Berlin: Walter de Gruyter, 1985.

23. Puchta R., Walther D., März M., Begel S., van Eldik R. Z. Anorg. Allg. Chem. 2019, 645, 701-705.
https://doi.org/10.1002/zaac.201800448

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Host-Guest Complexes of Two Isomeric 2,2’-Bioxazole Based {2}-Lehn-Type Cryptands. Prediction of Ion Selectivity by Quantum Chemical Calculations. Part XIV

References: