Issue 4, 2024

Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

Abstract

Cooperativity in hydrogen bonds can be crucial for the stabilization of supramolecular systems. In this contribution, we propose a simple covalent modification within a pyrazole-based trimeric rosette that significantly improves its binding strength. Using dispersion-corrected density functional theory, at the BLYP-D3(BJ)/6-311++(d,p) level, we show how an intramolecular hydrogen bond acts as a bridge between an electron-donating group and an electron-withdrawing group by moving the electron density from one group to the other one through the sigma electron system. This effect strongly enhances the inductive ability of the substituents, and further increases the synergy of the cyclic trimer.

Graphical abstract: Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

Supplementary files

Article information

Article type
Paper
Submitted
10 yan 2024
Accepted
23 fev 2024
First published
26 fev 2024

Mol. Syst. Des. Eng., 2024,9, 345-351

Augmentation of inductive effects through short range intramolecular hydrogen bonds for the improvement of cooperativity of trimeric rosettes

A. N. Petelski, T. Bundrea and N. M. Peruchena, Mol. Syst. Des. Eng., 2024, 9, 345 DOI: 10.1039/D4ME00008K

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