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Tepper R, Schulze B, Görls H, et al. Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors. Org Lett. 2015;17(23):5740-3doi: 10.1021/acs.orglett.5b02760.
Tepper, R., Schulze, B., Görls, H., Bellstedt, P., Jäger, M., & Schubert, U. S. (2015). Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors. Organic letters, 17(23), 5740-3. https://doi.org/10.1021/acs.orglett.5b02760
Tepper, Ronny, et al. "Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors." Organic letters vol. 17,23 (2015): 5740-3. doi: https://doi.org/10.1021/acs.orglett.5b02760
Tepper R, Schulze B, Görls H, Bellstedt P, Jäger M, Schubert US. Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors. Org Lett. 2015 Dec 04;17(23):5740-3. doi: 10.1021/acs.orglett.5b02760. Epub 2015 Nov 20. PMID: 26588346.
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Org Lett. 2015 Dec 04;17(23):5740-3. doi: 10.1021/acs.orglett.5b02760. Epub 2015 Nov 20.

Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors.

Organic letters

Ronny Tepper, Benjamin Schulze, Helmar Görls, Peter Bellstedt, Michael Jäger, Ulrich S Schubert

Affiliations

  1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena , Humboldtstrasse 10, 07743 Jena, Germany.
  2. Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena , Philosophenweg 7, 07743 Jena, Germany.
  3. Laboratory of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena , Lessingstrasse 8, 07743 Jena, Germany.

PMID: 26588346 DOI: 10.1021/acs.orglett.5b02760

Abstract

Preorganization via intramolecular hydrogen bonds was applied in a cleft-type receptor by exploiting the excellent halogen bond donor ability as well as hydrogen bond acceptor function of iodo-1,2,3-triazoles. As investigated by isothermal calorimetric titrations, the restriction of conformational freedom causes an enhanced entropic contribution resulting in a strongly increased binding affinity. This efficient way to improve the binding strength of 5-halo-1,2,3-triazoles paves the way for applications of new charge-neutral halogen bond donors in solution.

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