Issue 22, 2022

Assessing the effects of covalent, dative and halogen bonds on the electronic structure of selenoamides

Abstract

Here, the interaction between N,N-dimethyl-selenobenzoamide PhC([double bond, length as m-dash]Se)NMe2 (1) and various Lewis acids of different strengths, namely IC6F13(I), B(C6F5)3 (B) and Me+, has been analysed by a combined experimental and theoretical approach. In all cases, an increase of the C–NMe2 rotational barrier has been evidenced and quantified by 1H-variable temperature-exchange NMR spectroscopy (VT-EXSY) in the cases of 1-I and 1-B. For B(C6F5)3, the structure of the adduct has been elucidated by single crystal X-ray diffraction, allowing the lengthening of the Se–C bond (186 pm) and the consequent double characteristic of the C–NMe2 bond (131 pm) to be measured. Computational studies (mainly natural bond orbitals and natural orbital for chemical valence analyses) gave precious insight into the effect of various Lewis acids on the electronic structure of 1. The advantages and the limitations of this new method to characterize chemical interactions are discussed.

Graphical abstract: Assessing the effects of covalent, dative and halogen bonds on the electronic structure of selenoamides

Supplementary files

Article information

Article type
Paper
Submitted
23 3 2022
Accepted
03 5 2022
First published
03 5 2022

New J. Chem., 2022,46, 10568-10576

Assessing the effects of covalent, dative and halogen bonds on the electronic structure of selenoamides

G. Ciancaleoni, F. Marchetti, C. Santi, O. Merlino and S. Zacchini, New J. Chem., 2022, 46, 10568 DOI: 10.1039/D2NJ01421A

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