Issue 26, 2022
From the journal:

Dalton Transactions

π-Delocalization in phosphaphthalimide and its ambident reactivity (O/P) toward main-group electrophiles†

Qi Shen,a   Jiashi Xua  and  Xiaodan Chen ORCID logo *a  

* Corresponding authors

a Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China
E-mail: chxdlzhsh@jnu.edu.cn

Abstract

The report on phosphaphthalimide (1), the phosphorus analogue of the phthalimide anion, dates back to forty years ago. However, the presence of π-delocalization between two-coordinated phosphorus centre and neighbouring carbonyl groups in 1 has been underestimated. Herein, sodium salts of 1 were obtained through a convenient procedure on a relatively large scale with a modified procedure. Reactivity studies demonstrated that 1 is indeed a good electrophile and the essential role of π-delocalization in 1 controlling its ambident properties. NBO analysis revealed the p–π conjugation and p–σ* hyperconjugation in 1 affecting its bond lengths in opposite ways.

Graphical abstract: π-Delocalization in phosphaphthalimide and its ambident reactivity (O/P) toward main-group electrophiles

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2DT01163H
Article type
Paper
Submitted
14 Apr 2022
Accepted
03 Jun 2022
First published
07 Jun 2022

Dalton Trans., 2022,51, 10240-10248

Permissions

Request permissions

π-Delocalization in phosphaphthalimide and its ambident reactivity (O/P) toward main-group electrophiles

Q. Shen, J. Xu and X. Chen, Dalton Trans., 2022, 51, 10240 DOI: 10.1039/D2DT01163H

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