Citation: Bin-Bin YUAN, Jin-Shuai SONG, Xue-Yuan YAN, Han XIAO, Chun-Sen LI. Theoretical Study of Electronic Structure, Formation Mechanism and Intramolecular Sulfoxide Imidation Reactivity of Iron Phthalocyanine Nitrene Complex[J]. Chinese Journal of Structural Chemistry, ;2021, 40(4): 415-423. doi: 10.14102/j.cnki.0254-5861.2011-2956 shu

Theoretical Study of Electronic Structure, Formation Mechanism and Intramolecular Sulfoxide Imidation Reactivity of Iron Phthalocyanine Nitrene Complex

Bin-Bin YUAN ^{a, b} ,
Jin-Shuai SONG ^a,, ,
Xue-Yuan YAN ^{a, b} ,
Han XIAO ^{a, b} ,
Chun-Sen LI ^{a, b, c,,}

a.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, Xiamen 361005, China

Corresponding author: Jin-Shuai SONG, jssong@zzu.edu.cn Chun-Sen LI, chunsen.li@fjirsm.ac.cn
Received Date: 20 July 2020
Accepted Date: 12 October 2020

Fund Project: the NSFC 21933009the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000

Figures(8)

Density functional theory (DFT) calculations are performed to investigate recent experimentally studied ring-closing sulfoxide imidation catalyzed by Fe(Ⅱ)-phthalocyanine (Fe^ⅡPc). Our results reveal that the ground state of iron phthalocyanine nitrene intermediate (PcFeNR, R = (CH₂)₃(SO)Ph), which is believed to mediate the intramolecular imitation, is triplet state featuring a diradical structure. The formation of PcFeNR is the result of a denitrification process with a calculated high-barrier of 23.4 kcal/mol which is in good agreement with the experimentally observed high reaction temperature of 100 ℃. The generated PcFeNR undergoes a low-barrier intramolecular nucleophilic attack by proximal nitrogen atom on the sulfur accomplishing the cyclization of sulfoxide. This study provides theoretical insights into the mechanism-based design of useful catalysts for nitrene transfer reactions.
- nitrene transfer,
- sulfoxide cyclization,
- iron phthalocyanine,
- DFT,
- reaction mechanism
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