The fluorination of 2,4,5-trichloro-6-methylpyrimidine; Experimental study and CNDO/2 calculation |
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| Affiliation: | 1. Department of Neurosurgery, Tianjin Medical University General Hospital, Laboratory of Neuro-Oncology, Tianjin Neurological Institute, Key Laboratory of Post-trauma Neuro-repair and Regeneration in Central Nervous System, Ministry of Education, Tianjin Key Laboratory of Injuries, Variations and Regeneration of Nervous System, Tianjin 300052, China;2. Chinese Glioma Cooperative Group (CGCG), 6 Tiantanxi Li, Beijing 100050, China;3. Department of Molecular Neuropathology, Beijing Neurosurgical Institute, Capital Medical University, 6 Tiantanxi Li, Beijing 100050, China;4. Department of Medicine, Department of Surgery, The University of Oklahoma Health Sciences Center, Oklahoma City, OK 73104, United States;5. School of Materials Science and Engineering, Tianjin University, Tianjin 300072, China;1. Department of Civil Engineering, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, China;2. Engineered Materials Concepts, LLC, Charlottesville, VA 22901, USA;3. Engineering Technology Associates, Inc, 1133 E Maple Rd, Troy, MI 48083, USA;4. Central South University, Changsha, Hunan, 410083, P.R. China;5. School of Mechanical Engineering, Xi''an Jiaotong University, Xi''an, Shaanxi 710049, China;1. Fujian Provincial Key Laboratory of Innovative Drug Target Research and State Key Laboratory of Cellular Stress Biology, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, China;2. Department of Hepatobiliary Disease, Fuzhou General Hospital (Donfang Hospital), Xiamen University, Fuzhou 350025, China;3. Institute of Materials Research and Engineering, A*STAR (Agency for Science, Technology and Research), 2 Fusionopolis Way, Innovis, #08-03, Singapore 138634, Singapore |
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| Abstract: | A study of the kinetics and mechanism of the fluorination of 2,4,5-trichloro-6-methylpyrimidine (TCMP) to form 2,4-difluoro-5-chloro-6-methylpyrimidine (DFCMP) in polar aprotic solvents with KF or NaF has been performed. The rate constants of the fluorination under various conditions were measured. This fluorination proceeds as a pseudo-first-order consecutive reaction. The values of the activation enthalpy Δ H≠, the activation entropy Δ S≠ and Arrhenius activation energy Δ Ea were evaluated and the influence of solvents, catalysts and fluorinating agents was discussed. The CNDO/2 method has been applied to the calculation of the reaction path of the fluorination and the energy levels of the components. The calculated results agree well with experimental observation. |
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