Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101
4-amino-7,8-dinitropyrazolo-[5,1-d][1,2,3,5]-tetrazine 2-oxide (BITE-101) outperforms the benchmark explosive HMX in all aspects, showing application prospects as a new generation of high energy density material. To obtain the thermal decomposition mechanism and key intermediates of BITE-101, the in...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
KeAi Communications Co. Ltd.
2025-03-01
|
| Series: | Energetic Materials Frontiers |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666647225000041 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850150081607499776 |
|---|---|
| author | Zi-xuan Yang Shuang-fei Zhu Hai Duan Rui-jun Gou Yang Liu Shu-hai Zhang |
| author_facet | Zi-xuan Yang Shuang-fei Zhu Hai Duan Rui-jun Gou Yang Liu Shu-hai Zhang |
| author_sort | Zi-xuan Yang |
| collection | DOAJ |
| description | 4-amino-7,8-dinitropyrazolo-[5,1-d][1,2,3,5]-tetrazine 2-oxide (BITE-101) outperforms the benchmark explosive HMX in all aspects, showing application prospects as a new generation of high energy density material. To obtain the thermal decomposition mechanism and key intermediates of BITE-101, the initial decay pathways were studied by using the M062X method for optimization and DLPNO-CCSD(T)/cc-pVTZ methods for energies. The energy barrier results showed that the nitro-nitrite isomerization was the lowest, indicating that this path was the most advantageous in the reaction of BITE-101. In addition, the H transfer reaction has a promoting effect on the ring-opening reaction. Additionally, the influence of functional group position on the initial decomposition mechanism of energetic materials is also discussed. The results show that the most likely first decay paths are all caused by the functional groups on the tetrazine ring, and the position of the amino group had a great influence on the ring-opening reaction. These reactions can be clearly seen from the changes in ELF and Mayer bond order. These results will certainly deepen our understanding of the decay mechanism of pyrazolo-tetrazine. |
| format | Article |
| id | doaj-art-bfa20f3083494a068235ee12c95e879e |
| institution | OA Journals |
| issn | 2666-6472 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Energetic Materials Frontiers |
| spelling | doaj-art-bfa20f3083494a068235ee12c95e879e2025-08-20T02:26:40ZengKeAi Communications Co. Ltd.Energetic Materials Frontiers2666-64722025-03-0161425010.1016/j.enmf.2025.01.004Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101Zi-xuan Yang0Shuang-fei Zhu1Hai Duan2Rui-jun Gou3Yang Liu4Shu-hai Zhang5School of Environment and Safety Engineering, North University of China, Taiyuan, 030051, ChinaSchool of Environment and Safety Engineering, North University of China, Taiyuan, 030051, China; Corresponding author.Shaanxi Qinghua Vehicle Safety Systems Co.,Ltd, ChinaSchool of Environment and Safety Engineering, North University of China, Taiyuan, 030051, ChinaSchool of Environment and Safety Engineering, North University of China, Taiyuan, 030051, ChinaSchool of Environment and Safety Engineering, North University of China, Taiyuan, 030051, China; Corresponding author.4-amino-7,8-dinitropyrazolo-[5,1-d][1,2,3,5]-tetrazine 2-oxide (BITE-101) outperforms the benchmark explosive HMX in all aspects, showing application prospects as a new generation of high energy density material. To obtain the thermal decomposition mechanism and key intermediates of BITE-101, the initial decay pathways were studied by using the M062X method for optimization and DLPNO-CCSD(T)/cc-pVTZ methods for energies. The energy barrier results showed that the nitro-nitrite isomerization was the lowest, indicating that this path was the most advantageous in the reaction of BITE-101. In addition, the H transfer reaction has a promoting effect on the ring-opening reaction. Additionally, the influence of functional group position on the initial decomposition mechanism of energetic materials is also discussed. The results show that the most likely first decay paths are all caused by the functional groups on the tetrazine ring, and the position of the amino group had a great influence on the ring-opening reaction. These reactions can be clearly seen from the changes in ELF and Mayer bond order. These results will certainly deepen our understanding of the decay mechanism of pyrazolo-tetrazine.http://www.sciencedirect.com/science/article/pii/S2666647225000041Quantum chemistryPyrazolo-tetrazineDecomposition mechanismKey intermediatesFunctional groups |
| spellingShingle | Zi-xuan Yang Shuang-fei Zhu Hai Duan Rui-jun Gou Yang Liu Shu-hai Zhang Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 Energetic Materials Frontiers Quantum chemistry Pyrazolo-tetrazine Decomposition mechanism Key intermediates Functional groups |
| title | Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 |
| title_full | Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 |
| title_fullStr | Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 |
| title_full_unstemmed | Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 |
| title_short | Quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo-tetrazine: A case study of BITE-101 |
| title_sort | quantum chemistry modeling of the unimolecular decomposition mechanism and substituent effects of pyrazolo tetrazine a case study of bite 101 |
| topic | Quantum chemistry Pyrazolo-tetrazine Decomposition mechanism Key intermediates Functional groups |
| url | http://www.sciencedirect.com/science/article/pii/S2666647225000041 |
| work_keys_str_mv | AT zixuanyang quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 AT shuangfeizhu quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 AT haiduan quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 AT ruijungou quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 AT yangliu quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 AT shuhaizhang quantumchemistrymodelingoftheunimoleculardecompositionmechanismandsubstituenteffectsofpyrazolotetrazineacasestudyofbite101 |