Issue 21, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Jan 2019
Accepted
03 Apr 2019
First published
17 Apr 2019

New J. Chem., 2019,43, 8122-8131

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, 43, 8122 DOI: 10.1039/C9NJ00405J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements