title: Toward molecular recognition: three-point halogen bonding in the solid state and in solution.
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.
authors.affiliation: Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum , Universitätsstraße 150, 44801 Bochum, Germany.
authors.forename: Stefan H
authors.initials: SH
authors.lastname: Jungbauer
authors.forename: David
authors.initials: D
authors.lastname: Bulfield
authors.forename: Florian
authors.initials: F
authors.lastname: Kniep
authors.forename: Christian W
authors.initials: CW
authors.lastname: Lehmann
authors.forename: Eberhardt
authors.initials: E
authors.lastname: Herdtweck
authors.forename: Stefan M
authors.initials: SM
authors.lastname: Huber