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On the importance of antiparallel π–π interactions in the solid state of isatin-based hydrazides

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Abstract

The condensation of N-propyl isatin (1) with different carboxylic acid hydrazides (RCONHNH2 (2–6), R = arene) via sonication was used to synthesize five new hydrazones (7–11). Fully characterized molecular structures were further studied by single-crystal X-ray diffraction showing them to be Z-(syn-) form with respect to the hydrazoic C[double bond, length as m-dash]N bond. In the crystal structures, hydrogen bonds and π-stacking interactions are described and analyzed by means of density functional theory (DFT) calculations since they play a crucial role in the construction of three-dimensional supramolecular frameworks. Moreover, the noncovalent interactions have been characterized using the NCIplot index. Remarkably, the π-system of the substituted isatin ring presents a dual character (acidic/basic), thus promoting the formation of the antiparallel π-stacking assemblies to maximize electron donor–acceptor π–π interactions. Moreover, interesting cooperativity effects have been studied since the presence of an intramolecular H-bonding interaction enhances the strength of the π–π interactions as shown by DFT calculations.

Graphical abstract: On the importance of antiparallel π–π interactions in the solid state of isatin-based hydrazides

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Publication details

The article was received on 23 Jan 2019, accepted on 03 Apr 2019 and first published on 17 Apr 2019


Article type: Paper
DOI: 10.1039/C9NJ00405J
New J. Chem., 2019, Advance Article

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    On the importance of antiparallel π–π interactions in the solid state of isatin-based hydrazides

    M. N. Ahmed, M. Arif, F. Jabeen, H. A. Khan, K. A. Yasin, M. N. Tahir, A. Franconetti and A. Frontera, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ00405J

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