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- W2151833196 abstract "The 14-membered cyclic diamide 1,4,8,11-tetraazacyclotetradecane-5,12-dione (5,12-dioxocyclam) can be considered as a trans-autodiprotected tetraazamacrocycle and provides a convenient starting material for the preparation of macrobicyclic receptors. As an example, the secondary amine nitrogen atoms located at the 1 and 8 positions were cross-bridged with a 1,3-pyridyl strap, affording the constrained ansa-dioxocyclam ligand 1,9,12,18,22-pentaazatricyclo[7.6.6.13,7]docosa-3,5,7(22)-triene-13,19-dione (L1). The proton binding properties of this cage-type compound, which possesses a hemispherical cavity, were fully investigated by spectroscopic (IR, NMR, UV, MALDI-TOF MS), quantum chemical, and potentiometric methods. While both bridgehead tertiary amines have their free lone pairs oriented inside the cavity, intramolecular hydrogen bonding was found to play a key role in determining the structural features of the free base and its protonated forms. L1 behaves as a diprotic base in water with log K011 = 8.94(1) and log K012 = 2.32(9), but most interestingly shows slow proton-transfer rates on the NMR timescale." @default.
- W2151833196 created "2016-06-24" @default.
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- W2151833196 creator A5051818947 @default.
- W2151833196 date "2005-01-01" @default.
- W2151833196 modified "2023-09-27" @default.
- W2151833196 title "Synthesis, characterization and X-ray crystal structures of cyclam derivatives. Part VI. Proton binding studies of a pyridine-strapped 5,12-dioxocyclam based macrobicycle" @default.
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- W2151833196 doi "https://doi.org/10.1039/b410260f" @default.
- W2151833196 hasPublicationYear "2005" @default.
- W2151833196 type Work @default.