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 mar. 2022
Accepted
03 may. 2022
First published
03 may. 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

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