Issue 37, 2022

Understanding the n → π* non-covalent interaction using different experimental and theoretical approaches

Abstract

Herein, a perspective on the recent understanding of weak n → π* interaction obtained using different experimental and theoretical approaches is presented. This interaction is purely an orbital interaction that involves the delocalization of the lone pair electrons (n) on nitrogen, oxygen, and sulfur to the π* orbitals of C[double bond, length as m-dash]O, C[double bond, length as m-dash]N, and aromatic rings. The n → π* interaction has been found to profoundly influence the stabilization of peptides, proteins, drugs, and various small molecules. Although the functional properties of this non-covalent interaction are still quite underestimated, there are recent demonstrations of applying this interaction to the regulation of synthetic chemistry, catalysis, and molecular recognition. However, the identification and quantification of the n → π* interaction remain a demanding task as this interaction is quite weak and based on the electron delocalization between the two orbitals, while hyperconjugation interactions between neighboring atoms and the group involved in the n → π* interaction are simultaneously present. This review provides a comprehensive picture of understanding the n → π* interaction using different experimental approaches such as the X-ray diffraction technique, and electronic, NMR, microwave, and IR spectroscopy, in addition to quantum chemistry calculations. A detailed understanding of the n → π* interaction can help in modulating the strength of this interaction, which will be further helpful in designing efficient drugs, synthetic peptides, peptidomimetics, etc.

Graphical abstract: Understanding the n → π* non-covalent interaction using different experimental and theoretical approaches

Article information

Article type
Perspective
Submitted
06 ⵎⴰⵢ 2022
Accepted
27 ⵢⵓⵏ 2022
First published
29 ⵢⵓⵏ 2022

Phys. Chem. Chem. Phys., 2022,24, 22371-22389

Understanding the n → π* non-covalent interaction using different experimental and theoretical approaches

P. Panwaria and A. Das, Phys. Chem. Chem. Phys., 2022, 24, 22371 DOI: 10.1039/D2CP02070J

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