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Hydrogen Bonded Phenol-Quinolines with Highly Controlled Proton-Transfer Coordinate
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
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2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20, 3365-3372 p.Article in journal (Refereed) Published
Abstract [en]

A series of polycyclic phenols with intramolecular hydrogen bonds (IMHB) to quinolines was synthesized by Friedlander annulation of cycloalkanone-functionalized anisoles with 2-aminobenzaldehyde. The prepared compounds represent the first series of IMHB phenols in which the substitution and conjugation patterns between the phenols and the hydrogen bond acceptors are kept constant, and in which comparable electronic interaction between the two subunits is thus ensured. The distance and relative orientation between the phenolic OH and the quinolone nitrogen atom is controlled by 1,3-cycloalkadienes of different ring sizes to which the phenol and quinoline subunits are formally annulated. H-1 delta(OH) chemical shift and Xray crystal structure characterization support the conclusion that the size and conformational preference of the 1,3-cycloalkadiene rings control the H-bond geometry and strength. As a result, the oxygen to nitrogen distances differ by as much as 0.30ss the seri.

Place, publisher, year, edition, pages
2016. no 20, 3365-3372 p.
Keyword [en]
Hydrogen bonds, Donor-acceptor distance, Conjugation, Nitrogen heterocycles, Phenols
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-307960DOI: 10.1002/ejoc.201600460ISI: 000380138100015OAI: oai:DiVA.org:uu-307960DiVA: diva2:1049149
Funder
Swedish Research CouncilSwedish Energy AgencyKnut and Alice Wallenberg Foundation
Available from: 2016-11-23 Created: 2016-11-23 Last updated: 2016-11-23Bibliographically approved

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Glover, Starla D.Orthaber, AndreasHammarström, LeifOtt, Sascha
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Department of Chemistry - ÅngströmPhysical ChemistryMolecular Biomimetics
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