Host-guest complexes of two isomeric 2,2’-bioxazole based {2}-lehn-type cryptands. Prediction of ion selectivity by quantum chemical calculations. Part XIV

Ćoćić D, Siegl S, Manaa A, Begel S, Hubbard CD, Puchta R (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Journal Macroheterocycles Ivanovo State University of Chemistry and Technology

Book Volume: 13

Pages Range: 215-222

Journal Issue: 3 b

DOI: 10.6060/mhc200603p

Abstract

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.

Authors with CRIS profile

Svetlana Begel Lehrstuhl für Anorganische und Metallorganische Chemie Ralph Puchta Lehrstuhl für Anorganische und Metallorganische Chemie

Involved external institutions

Lothar-von-Faber-Schule - Staatliche Fachoberschule Nürnberg

Germany (DE) University of New Hampshire

United States (USA) (US)

How to cite

APA:

Ćoćić, D., Siegl, S., Manaa, A., Begel, S., Hubbard, C.D., & Puchta, R. (2020). Host-guest complexes of two isomeric 2,2’-bioxazole based {2}-lehn-type cryptands. Prediction of ion selectivity by quantum chemical calculations. Part XIV. Journal Macroheterocycles, 13(3 b), 215-222. https://dx.doi.org/10.6060/mhc200603p

MLA:

Ćoćić, Dušan, et al. "Host-guest complexes of two isomeric 2,2’-bioxazole based {2}-lehn-type cryptands. Prediction of ion selectivity by quantum chemical calculations. Part XIV." Journal Macroheterocycles 13.3 b (2020): 215-222.

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