The symmetry breaking phenomenon in 1,2,3-trioxolene and C2Y3Z2 (Z= O, S, Se, Te, Z= H, F) compounds: a pseudo Jahn−Teller origin study

The goal of this brief partly review paper is to summarize the results of the works published over the last few years regarding the origin of the out-of-plane distortions (puckering) of heterocyclic compounds. In all the papers devoted to this problem, it is shown that the instability of planar configurations of heterocyclic molecules leading to symmetry breaking and distortions is induced by the pseudo Jahn-Teller effect (PJTE). Special attention in this work is paid to the mechanism of suppression and enhancement of the PJTE distortions of heterocycles by oxidation, reduction, and chemical substitutions. It is demonstrated that oxidation of 1,4-dithiine containing compounds leads to suppression of the PJTE and to restoration of their planar nuclear configurations. An example of a dibenzo[1,2]dithiine molecule is used to demonstrate the mechanism of enhancement of the PJTE by reduction. It is shown that the reduction of the neutral C 12 H 8 S 2 molecule up to the dianion (C 12 H 8 S 2) 2− enhances the PJTE, followed by the S-S bond cleavage and significant structural distortions of the system. The change of the PJTE by chemical substitutions, accompanied either by puckering or by planarization of heterocyclic compounds, is discussed using as examples 1,4-ditinine and its S-oxygenated derivatives.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

The symmetry breaking phenomenon in 1,2,3-trioxolene and C2Y3Z2 (Z= O, S, Se, Te, Z= H, F) compounds: a pseudo Jahn−Teller origin study

Cited by 2 publications

References 38 publications

Manipulation of planar structure of 1,2,5- and 1,3,4-triazoles and the pseudo Jahn–Teller effect in their 1-pnictogen derivatives

Manipulation of planar structure of 1,2,5- and 1,3,4-triazoles and the pseudo Jahn–Teller effect in their 1-pnictogen derivatives

Pseudo Jahn-Teller Effect in Puckering and Planarization of Heterocyclic Compounds

Contact Info

Product

Resources

About