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  Toward Molecular Recognition: Three-Point Halogen Bonding in the Solid State and in Solution

Jungbauer, S. H., Bulfield, D., Kniep, F., Lehmann, C. W., Herdtweck, E., & Huber, S. M. (2014). Toward Molecular Recognition: Three-Point Halogen Bonding in the Solid State and in Solution. Journal of the American Chemical Society, 136(48), 16740-16743. doi:10.1021/ja509705f.

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 Creators:
Jungbauer, Stefan H.1, 2, Author
Bulfield, David1, Author
Kniep, Florian2, Author
Lehmann, Christian W.3, Author              
Herdtweck, Eberhardt2, Author
Huber, Stefan M.1, 2, Author
Affiliations:
1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany, ou_persistent22              
2Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany, ou_persistent22              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: A well-defined three-point interaction based solely on halogen bonding is presented. X-ray structural analyses of tridentate halogen bond donors (halogen-based Lewis acids) with a carefully chosen triamine illustrate the ideal geometric fit of the Lewis acidic axes of the former with the Lewis basic centers of the latter. Titration experiments reveal that the corresponding binding constant is about 3 orders of magnitude higher than that with a comparable monodentate amine. Other, less perfectly fitting multidentate amines also bind markedly weaker. Multipoint interactions like the one presented herein are the basis of molecular recognition, and we expect this principle to further establish halogen bonding as a reliable tool for solution-phase applications.

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Language(s): eng - English
 Dates: 2014-09-252014-11-192014-12-03
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja509705f
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 136 (48) Sequence Number: - Start / End Page: 16740 - 16743 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870