Quinoline-2-carbaldehyde

Motswainyana, William M.; Onani, Martin O.

doi:10.1107/s1600536811035653

Cited by 2 publications

(1 citation statement)

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“…The quinolinecarboxaldehydes have also been found to exhibit relevant biological properties, in particular, antimicrobial activity. − From a more fundamental perspective, they have been reported to present interesting physicochemical properties, which have mostly been assigned to the presence of the conformationally flexible aldehyde substituent and, in the solid state, also to the presence of weak π···π and C–H···π contacts and C–H···O hydrogen-bond-type intermolecular interactions. − For isolated molecules, the intramolecular degree of freedom associated with internal rotation of the aldehyde substituent plays the major role in determining conformationally related properties of such compounds.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Matrix-Isolation FTIR, and UV-Induced Conformational Isomerization of 3-Quinolinecarboxaldehyde

et al. 2014

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The crystal structure of 3-quinolinecarboxaldehyde (3QC) has been solved, and the compound has been shown to crystallize in the space group P21/c (monoclinic) with a = 6.306(4), b = 18.551(11), c = 6.999(4) Å, β = 106.111(13)°, and Z = 4. The crystals were found to exhibit pseudomerohedral twinning with a twin law corresponding to a two-fold rotation around the monoclinic (100) reciprocal lattice axis (or [4 0 1] in direct space). Individual molecules adopt the syn conformation in the crystal, with the oxygen atom of the aldehyde substituent directed toward the same side of the ring nitrogen atom. In the gas phase, the compound exists in two nearly isoenergetic conformers (syn and anti), which could be successfully trapped in solid argon at 10 K, and their infrared spectra are registered and interpreted. Upon in situ irradiation of matrix-isolated 3QC with UV light (λ > 315 nm), significant reduction of the population of the less stable anti conformer was observed, while that of the conformational ground state (syn conformer) increased, indicating occurrence of the anti → syn isomerization. Upon irradiation at higher energy (λ > 235 nm), the syn → anti reverse photoreaction was observed. Interpretation of the structural, spectroscopic, and photochemical experimental data received support from quantum chemical theoretical results obtained at both DFT/B3LYP (including TD-DFT investigation of excited states) and MP2 levels, using the 6-311++G(d,p) basis set.

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