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Substituent effects on the crystallization mechanisms of 7-chloro-4-substituted-quinolines

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Abstract

The crystallization mechanisms of a series of fourteen 7-chloro-4-substituted-quinolines (substituents: (1) OCH3, (2) OCH2CH3, (3) OCH2CH[double bond, length as m-dash]CH2, (4) O(CH2)2OH, (5) O(CH2)3OH, (6) NH(CH2)2CH3, (7) NH(CH2)3CH3, (8) NH(CH2)2OH, (9) NHCH(CH2CH3)CH2OH, (10) NH(CH2)2Cl, (11) NHN[double bond, length as m-dash]CH(C6H5), (12) NHN[double bond, length as m-dash]CH(2-FC6H4), (13) NHN[double bond, length as m-dash]CH(3-FC6H4), and (14) NHN[double bond, length as m-dash]CH(4-FC6H4)) were proposed based on a retrocrystallization approach using the supramolecular cluster as demarcation. Crystallization mechanism stage parameters – NCG% and NG/NC – were determined. The 4-substituents present in quinolines caused six different mechanisms, starting from the monomers in solution to dimers, 1D nuclei, and 2D nuclei (6, 11, 12); 2D nucleus formation (5); 1D nuclei to 2D nuclei (7, 9); concomitant dimers and 1D nuclei to a 3D crystal (8); 1D nuclei directly to a 3D crystal lattice (1–4, 10, 14), and dimers to 2D nuclei and then to a 3D crystal (13). Analysis of GAI showed atom⋯atom intermolecular interactions in the proposed first nuclei for compounds 4 and 5. The nucleation process inferred in the solid state was partially confirmed during the formation of the proto-crystal in solution due to the changes of the hydrogen chemical shift in variable-concentration 1H-NMR experiments. Results revealed that the size of the alkyl chain and the presence of different functional groups in the 4-substituents influenced the crystallization process.

Graphical abstract: Substituent effects on the crystallization mechanisms of 7-chloro-4-substituted-quinolines

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Supplementary files

Article information


Submitted
11 Feb 2020
Accepted
19 Apr 2020
First published
20 Apr 2020

CrystEngComm, 2020, Advance Article
Article type
Paper

Substituent effects on the crystallization mechanisms of 7-chloro-4-substituted-quinolines

J. P. P. Copetti, P. R. S. Salbego, T. Orlando, J. M. L. Rosa, G. F. Fiss, J. P. G. de Oliveira, M. L. A. A. Vasconcellos, N. Zanatta, H. G. Bonacorso and M. A. P. Martins, CrystEngComm, 2020, Advance Article , DOI: 10.1039/D0CE00214C

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