Local dipole interactions induce helicity of (<Emphasis Type="Italic">S</Emphasis>)-2-butyl-<Emphasis Type="Italic">N</Emphasis>-(1,8-naphthaloyl)-2-aminobenzoate molecules containing 1,8-naphthalimide rings utilized as a column building blocks: X-ray and quantum mechanical studies |
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Authors: | Agnieszka Plutecka Marcin Hoffmann Urszula Rychlewska |
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Institution: | (1) Department of Crystallography, Adam Mickiewicz University, Grunwaldzka 6, Poznan, 60780, Poland;(2) Quantum Chemistry Group Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznan, 60780, Poland |
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Abstract: | In the crystal of triclinic symmetry the title compound contains four independent molecules, which differ in the conformation
of the aliphatic carbon chain (T, G
+and G
−) and in the helicity (M or P) of the N-(1,8-naphthaloyl)-2-aminobenzoate (NAB) unit. Quantum chemical MP2 calculations showed that isolated molecules favor helicity
of NAB bichromophores most likely due to attractive interactions between local dipoles formed along carbonyl bonds, such that
the helical arrangement of O=C–C–C–N–C=O fragments is stabilized by intramolecular interactions between terminal anti-parallel
local carbonyl dipoles. In the crystal structure, columnar stacking of the anti-parallel 1,8-naphalimide rings is observed.
In a column the neighboring NAB units display opposite helicity. |
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Keywords: | Dipolar interactions Stacking interactions Helicity 1 8-Naphthalimides Bichromophores Derivatives of chiral alcohols |
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