Citation: SUN Ying, REN Ai-Min, MIN Chun-Gang, ZOU Lu-Yi, REN Xue-Feng. Theoretical Investigation of the Key Reaction for the Chemiluminescence of Cypridina Luciferin Analogues[J]. Acta Physico-Chimica Sinica, ;2010, 26(10): 2779-2786. doi: 10.3866/PKU.WHXB20101018 shu

Theoretical Investigation of the Key Reaction for the Chemiluminescence of Cypridina Luciferin Analogues

1.
State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University,Changchun 130023, P. R. China

Received Date: 7 June 2010
Available Online: 27 September 2010
Fund Project: 国家自然科学基金(20673045, 20973078) (20673045, 20973078) 留学回国人员启动基金(外交司留(2008)890 号) (外交司留(2008)890 号)国家重点基础研究发展计划项目(973)(2002CBN613406) 资助 (973)(2002CBN613406)

A series of 6-aryl-2-methylimidazo[1,2-α]pyrazin-3-(7H)-ketone based derivatives MIPa-MIPd (cypridina luciferin analogues) were investigated using the B3LYP/6-311+G(d,p) method, and we modeled a 6-site replacement by different substituents. The effect of different substitutions on cypridina luciferin analogues in their transition from anions to free radicals was studied by electron extraction potentials (EEP) and natural charge population analysis (NPA) in gas phase, dimethyl sulfoxide (DMSO), and diglyme (DG). The calculated results indicated that MIPb (3-indolyl as the substituent) had a lower EEP and a larger natural charge population change occurred at the MIP moiety in DG when transitioning from the anion to its free radical than in the other solvents. We also showed that 3-indolyl, as a substituent, accelerated the luminescent reaction of MIP.
- Density functional theory,
- Cypridina luciferin,
- Chemiluminescence,
- Electron extraction potential,
- Natural charge population analysis
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