Citation: Gai-Mei LIU, Wei-Jia MA, Yan WANG, Yan YANG, Xin-Jian SONG. Computational Insights into the Excited State Intramolecular Proton Transfer Reactions in Ortho-hydroxylated Oxazolines[J]. Chinese Journal of Structural Chemistry, ;2021, 40(5): 540-548. doi: 10.14102/j.cnki.0254–5861.2011–2990 shu

Computational Insights into the Excited State Intramolecular Proton Transfer Reactions in Ortho-hydroxylated Oxazolines

Gai-Mei LIU ^a ,
Wei-Jia MA ^a ,
Yan WANG ^{a, b,,} ,
Yan YANG ^a ,
Xin-Jian SONG ^a

a.
School of Chemistry and Environmental Engineering, Hubei Minzu University, Enshi 445000, China
b.
Key Laboratory of Magnetic Resonance in Biological Systems, National Center for Magnetic Resonance in Wuhan, State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, China

Corresponding author: Yan WANG, hbmdwangy@aliyun.com
Received Date: 22 September 2020
Accepted Date: 7 December 2020

Fund Project: the National Natural Science Foundation of China 21963008the National Natural Science Foundation of China 21767010the Natural Science Foundation of Hubei Province 2018CFB650the Postgraduate Research and Innovation Plan Project of Hubei Minzu University MYK2020001

Figures(5)

Excited-state intramolecular proton transfer (ESIPT) reactions of three ortho-hydroxylated oxazolines, 2-(4, 4-dimethyl-4, 5-dihydro-oxazol-2-yl)-phenol (DDOP), 4-(4, 4-dimethyl-4, 5-dihydro-oxazol-2-yl)-[1, 1΄-biphenyl]-3-ol (DDOP-C₆H₅) and 4-(4, 4-dimethyl-4, 5-dihydrooxazol-2-yl)-3-hydroxy-benzonitrile (DDOP-CN), have been systematically explored by density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods. Two stable configurations (enol and keto forms) are found in the ground states (S₀) for all the compounds while the enol form only exists in the first excited states (S₁) for the compound modified with electron donating group (-C₆H₅). In addition, the calculated absorption and emission spectra of the compounds are in good agreements with the experiments. Infrared vibrational spectra at the hydrogen bond groups demonstrate that the intramolecular hydrogen bond O(1)−H(2)···N(3) in DDOP-C₆H₅ is strengthened in the S₁ states, while the frontier molecular orbitals further reveal that the ESIPT reactions are more likely to occur in the S₁ states for all the compounds. Besides, the proton transfer potential energy curves show that the enol forms can barely convert into keto forms in the S₀ states because of the high energy barriers. Meanwhile, intramolecular proton transfer of all the compounds could occur in S₁ states. The ESIPT reactions of the ortho-hydroxylated oxazolines are barrierless processes for unsubstituted DDOP and electron withdrawing substituted DDOP-CN, while the electron donating substituted DDOP-C₆H₅ has a small barrier, so the electron donating is unfavorable to the ESIPT reactions of ortho-hydroxylated oxazolines.
- excited-state intramolecular proton transfer,
- electron donating group,
- ortho-hydroxylated oxazolines,
- potential energy curves
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