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Solid-state NMR and x-ray diffraction studies of ionic complex of 1,8-bis(dimethylamino)naphthalene (DMAN) with picrolonic acid

✍ Scribed by Krzysztof Woźnaik; Tadeusz Marek Krygowski; Dorota Pawlak; Walaw Kolodziejski; Eugeniusz Grech

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 200 KB
Volume: 10
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199711)10:11<814::aid-pca953>3.0.co;2-s

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✦ Synopsis

An ionic complex of 1,8-bis(dimethylamino)naphthalene with picrolonic acid was studied by C and 1 H magic angle spinning and x-ray diffraction. Structural and spectroscopic features of this compound were investigated. The detailed x-ray structure of this complex is described. A multicentre model of hydrogen bonding in proton sponges {[Me 2 N-H • • • NMe 2 ] + • • • X ␦Ϫ } is proposed and the influence of weak intermolecular intractions with the nearest electronegative atom in crystal lattice of a proton sponge on the strong intramolecular [N-H • • • N] + hydrogen bonding is demonstrated. It appears that weak interactions of electronegative atoms with the nearest methyl hydrogen atoms can influence the localization of the proton in the intramolecular [N-H • • • N] + hydrogen bridge.

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