Structural Chemistry

, Volume 30, Issue 1, pp 303–316 | Cite as

Instability of two–dimensional structure of dichalcogenin and dipnictogenin octa–heterocyclic systems with 1,2–C6X2(X = O, S, Se, Te, N, P) unsaturated rings

  • Ali Reza IlkhaniEmail author
Original Research


The planar configuration and twisted structures of the dichalcogenin (DCG) and dipnictogenin (DPG) octa–heterocyclic systems with 1,2–C6X2 ring in their main skeleton were computed through ab initio geometry optimization and following frequency calculations. Whereas the C6X2 eight–membered unsaturated rings in the considered compounds are unstable in their planar configurations, the molecules distorted from their planar shape with C2v, high symmetry into the C2, lower symmetry, twisted equilibrium configuration. Based on adiabatic potential energy surface (APES) cross sections, coupling between the ground state (1A1) and 1A2 excited state and the PJTE (1A1 + 1A2 + ···) ⊗ a2 are the reasons for the C6X2 unsaturated rings’ two–dimensional structure instability. Moreover, substitution of two hydrogen atoms in bonding with nitrogen and phosphorus positions of DPGs with halogens significantly changed the effect in the 1,2–diazocine and 1,2–diphosphocine compounds. Furthermore, intramolecular hydrogen bonding in the systems with 1,2–C6X2 (X = O, N) rings affect two–dimensional instability of the molecular structure.


PJTE Non–planarity in eight–membered rings Symmetry breaking phenomena 2D octa–heterocyclics 


Funding information

The author is thankful to Yazd Branch, Islamic Azad University for their financial support of this work. This research has been enabled in part with support from Westgrid ( and Compute/Calcul Canada (

Compliance with ethical standards

Conflict of interest

The author declares that he has no competing interests.


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Authors and Affiliations

  1. 1.Department of Chemistry, Yazd BranchIslamic Azad UniversityYazdIran
  2. 2.Department of ChemistryUniversity of AlbertaEdmontonCanada

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