Citation: GÜL Vedat, IŞIN Dilara Özbakir. Computational Investigation of the Substituent Effect on the Intramolecular Proton Transfer Reaction of 3-Hydroxytropolone[J]. Chinese Journal of Structural Chemistry, ;2014, 33(12): 1757-1767. doi: 10.14102/j.cnki.0254-5861.2010-1628 shu

Computational Investigation of the Substituent Effect on the Intramolecular Proton Transfer Reaction of 3-Hydroxytropolone

GÜL Vedat ,
IŞIN Dilara Özbakir ^,

1.
Chemistry Department, Faculty of Science, Cumhuriyet University 58140 Sivas, Turkey

Corresponding author: IŞIN Dilara Özbakir,
Received Date: 2 August 2014
Available Online: 20 October 2014

The effects of substituent type and position on the proton transfer reaction of 3-hydroxytropolone (3-OHTRN) have been investigated theoretically by using density functional theory at the level of B3LYP/6-31+G** method. The influence of solvent on the proton transfer reactions of substituted 3-OHTRN has been examined using the self-consistent isodensity polarized continuum model (SCI-PCM) in water. As a result, while the proton transfer reaction is kinetically the easiest by substitution on position 3 of -NH₂ group in the gas phase, it is kinetically the easiest by substitution on position 5 of the same group in water. In addition, these reactions are either kinetically or thermodynamically easier in the gas phase than that in water, except the reaction of structure with -NH₂ group at position 6.
- tropolone derivative,
- 3-hydroxytropolone,
- the proton transfer reaction,
- density functional theory
1. [1]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
2. [2]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429
3. [3]
  Haifeng ZHENG , Xingzhe GUO , Yunwei WEI , Xinfang WANG , Huimin QI , Yuting YAN , Jie ZHANG , Bingwen LI . Post-synthetic modification strategy to construct Co-MOF composites for boosting oxygen evolution reaction activity. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 193-202. doi: 10.11862/CJIC.20250029
4. [4]
  Xu Huang , Kai-Yin Wu , Chao Su , Lei Yang , Bei-Bei Xiao . Metal-organic framework Cu-BTC for overall water splitting: A density functional theory study. Chinese Chemical Letters, 2025, 36(4): 109720-. doi: 10.1016/j.cclet.2024.109720
5. [5]
  Dixing Ni , Jiarui Qi , Zhi Deng , Dong Ding , Rui Wang , Wenjie Zhou , Sisi Zhou , Yang Sun , Shuai Li , Zhaoxiang Wang . Voltage design and transport channel optimization of anti-perovskite cathode materials: A density functional theory study. Chinese Chemical Letters, 2025, 36(12): 110683-. doi: 10.1016/j.cclet.2024.110683
6. [6]
  Zhihao Li , Zhiruo Zhou , Yuan Qin , Dan Huang , Meizhen Wang . Density functional theory assists in promoting advanced oxidation processes: Toward efficient antibiotic degradation in waters. Chinese Chemical Letters, 2026, 37(6): 112318-. doi: 10.1016/j.cclet.2025.112318
7. [7]
  Hongen Cao , Xinrui Xiao , Xu Zhang , Yiyang Zhang , Lei Yu . Element Transfer Reaction theory: Scientific connotation and its applications in chemical industry. Chinese Chemical Letters, 2025, 36(9): 110924-. doi: 10.1016/j.cclet.2025.110924
8. [8]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
9. [9]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
10. [10]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
11. [11]
  Yupeng TANG , Haiying YANG , Fan JIN , Nan LI . Hydrogen storage properties of C₆S₆Li₆: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1827-1839. doi: 10.11862/CJIC.20240460
12. [12]
  Hao Sun , Chenzi Li , Wanting Yu , Yang Chen , Zhe Sun , Zhuofei Li , Wei Huang , Dayu Wu , Liangliang Zhu . Excited-state intramolecular proton transfer (ESIPT)-triggered photochromic materials. Chinese Chemical Letters, 2026, 37(6): 111971-. doi: 10.1016/j.cclet.2025.111971
13. [13]
  Heng-Su Liu , Xi-Ming Zhang , Ge-Hao Liang , Shisheng Zheng , Jian-Feng Li . Investigation of water structure and proton transfer within confined graphene by ab initio molecule dynamics and multiscale data analysis. Chinese Journal of Structural Chemistry, 2025, 44(6): 100596-100596. doi: 10.1016/j.cjsc.2025.100596
14. [14]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
15. [15]
  Jiawei Ge , Xian Wang , Heyuan Tian , Hao Wan , Wei Ma , Jiangying Qu , Junjie Ge . Iridium-based catalysts for oxygen evolution reaction in proton exchange membrane water electrolysis. Chinese Chemical Letters, 2025, 36(5): 109906-. doi: 10.1016/j.cclet.2024.109906
16. [16]
  Guanjun Chen , Jiayi Yang , Zheming Huang , Long Chen , Wenyuan Duan , Tong Wang , Xingang Kong , Haibo Yang . Engineering the interlayer sodium density in layered sodium cobalt oxide for boosted chlorine evolution reaction. Chinese Chemical Letters, 2025, 36(12): 111662-. doi: 10.1016/j.cclet.2025.111662
17. [17]
  Kun Zhang , Lei Wu , Kaixi Lan , Yanting Zhang , Wenxin Zhang , Huanhuan Li , Guoji Huang , Dongshuang Wu , Long Chen , Manni Li . N-3 of 1-methylimidazole: Enhancing proton conduction in COF under humidity conditions. Chinese Chemical Letters, 2026, 37(6): 111043-. doi: 10.1016/j.cclet.2025.111043
18. [18]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
19. [19]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
20. [20]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1783)
HTML views(51)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return