Dynamic Covalent Bonds in the Ebselen Class of Antioxidants Probed by X-ray Quantum Crystallography

A Singh, K Avinash, LA Malaspina, M Banoo, K Alhameedi, D Jayatilaka, S Grabowsky, SP Thomas

Research output: Contribution to journalArticlepeer-review

1 Citation (Web of Science)


Dynamic bonds are essential structural ingredients of dynamic covalent chemistry that involve reversible cleavage and formation of bonds. Herein, we explore the electronic characteristics of Se−N bonds in the organo-selenium antioxidant ebselen and its derivatives for their propensity to function as dynamic covalent bonds by employing high-resolution X-ray quantum crystallography and complementary computational studies. An analysis of the experimentally reconstructed X-ray wavefunctions reveals the salient electronic features of the Se−N bonds with very low electron density localized at the bonding region and a positive Laplacian value at the bond critical point. Bond orders and percentage covalency and ionicity estimated from the X-ray wavefunctions, along with localized orbital locator (LOL) and electron localization function (ELF) analyses show that the Se−N bond is unique in its closed shell-like features, despite being a covalent bond. Time-dependent DFT calculations simulate the cleavage of Se−N bonds in ebselen in the excited state, further substantiating their nature as dynamic bonds.
Original languageEnglish
Article numbere202303384
Number of pages10
Issue number14
Early online date21 Dec 2023
Publication statusPublished - 7 Mar 2024


Dive into the research topics of 'Dynamic Covalent Bonds in the Ebselen Class of Antioxidants Probed by X-ray Quantum Crystallography'. Together they form a unique fingerprint.

Cite this