Quantum chemical study on isomerization and transformation of hexabromocyclododecanes

  • Haijie CaoEmail author
  • Shijie Wu
  • Maoxia HeEmail author
Original Research


Hexabromocyclododecanes (HBCDs) have been frequently detected in environment. The isomerization between HBCDs and thermodynamic properties of unimolecular and bimolecular decomposition reactions of (−)-α-HBCD and (−)-γ-HBCD have been investigated using the quantum chemical method. The results show that isomerization via 1,2-shift of Br atoms occurs between the (−)-α/(−)-γ, (+)-α/(+)-γ, and (+)-β/(−)-β counterparts of HBCDs. Self-decomposition of HBCDs to pentabromocyclododecenes and HBr progresses slowly at low temperature but becomes competitive with the isomerization reactions at high temperature. The generated products are also toxic pollutants to the aquatic organisms. The reaction of two commonly detected HBCDs, (−)-γ-HBCD and (−)-α-HBCD, with OH radical and H atom have been studied. (−)-γ-HBCD has bigger rate constants in the reaction with OH radical and H atom than (−)-α-HBCD all over studied temperature. After a series of unimolecular or bimolecular reactions, the formed pentabrominated intermediate can decompose into ethane, vinyl bromide, and 1,2-dibromoethylene after sufficient heat adsorption.


HBCDs Isomerization Decomposition Rate constants Toxicity 


Funding information

This work was supported financially by the National Natural Science Foundation of China (21477065, 21077067, and 21103147), the China Postdoctoral Science Foundation (2017 M610409), the Taishan Scholars Advantageous and Distinctive Discipline Program, and the Taishan Scholar Program of Shandong Province, China.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11224_2018_1244_MOESM1_ESM.docx (2.3 mb)
ESM 1 The additional information, including the geometry structures, relative energy data, the CTST rate constants as noted in the text, are shown in Supplementary Material. (DOCX 2389 kb)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Materials for Energy and Environment, School of Materials Science and EngineeringQingdao UniversityQingdaoPeople’s Republic of China
  2. 2.Environment Research InstituteShandong UniversityJinanPeople’s Republic of China

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