Issue 60, 2020

How does excited-state antiaromaticity affect the acidity strengths of photoacids?

Abstract

Photoacids like substituted naphthalenes (X = OH, NH3+, COOH) are aromatic in the S0 state and antiaromatic in the S1 state. Nucleus independent chemical shifts analyses reveal that deprotonation relieves antiaromaticity in the excited conjugate base, and that the degree of “antiaromaticity relief” explains why some photoacids are stronger than others.

Graphical abstract: How does excited-state antiaromaticity affect the acidity strengths of photoacids?

Supplementary files

Article information

Article type
Communication
Submitted
23 Agd 2020
Accepted
18 Cax 2020
First published
27 Cax 2020

Chem. Commun., 2020,56, 8380-8383

Author version available

How does excited-state antiaromaticity affect the acidity strengths of photoacids?

Z. Wen, L. J. Karas, C. Wu and J. I. Wu, Chem. Commun., 2020, 56, 8380 DOI: 10.1039/D0CC02952A

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