溶剂调控2-(2'-羟基-5'-硝基)苯基苯并咪唑的基态结构
A Study on Structure of Solvent Mediated 2-(2'-Hydroxyphenyl-5'-Nitro)Be-Nzimidazole
摘要: 通过2-(2'-羟基-5'-硝基)苯基苯并咪唑(HBI-pNO2)在苯、四氢呋喃、乙腈及甲醇中的稳态吸收光谱，结合密度泛函理论及含时密度泛函理论计算确定了，非极性溶剂中，HBI-pNO2以顺式醇构型存在于基态。借助HBI-pNO2在碱性环境中的稳态吸收光谱确定了，在极性溶剂甲醇中，HBI-pNO2在长波长处的吸收带对应于阴离子的吸收。实验结合理论计算指认了其阴离子结构。
Abstract: We obtained the UV absorption spectra of 2-(2'-hydroxy-5'-nitro)phenylbenzimidazole (HBI-pNO2) in benzene, tetrahydrofuran, acetonitrile and methanol. Combining with DFT and TDDFT calculations, we further determined the structures of HBI-pNO2 as enol in nonpolar solvents. According to comparing the absorption spectra ofHBI-pNO2 in base solutions, we concluded the maximum absorption band of HBI-pNO2 in polar solvents was ascribed to the absorbance of anion. Combining with DFT and TDDFT calculations, we further determined the structure of anion in polar solvents.
文章引用：岳倩倩, 赵彦英. 溶剂调控2-(2'-羟基-5'-硝基)苯基苯并咪唑的基态结构[J]. 物理化学进展, 2022, 11(2): 69-77. https://doi.org/10.12677/JAPC.2022.112010

参考文献

[1] Andrés-Bello, A., Barreto-Palacios, V., García-Segovia, P., et al. (2013) Effect of pH on Color and Texture of Food Products. Food Engineering Reviews, 5, 158-170. [Google Scholar] [CrossRef] 
[2] Indiarto, R., Nurhadi, B., Tensiska, T., et al. (2020) Effect of Liquid Smoke on Microbiological and Physico-Chemical Properties of Beef Meatballs during Storage. Food Research, 4, 522-531. [Google Scholar] [CrossRef] 
[3] Jin, Q. and Kirk, M.F. (2018) pH as a Primary Control in Environmental Microbiology: 1. Thermodynamic Perspective. Frontiers in Environmental Science, 6, 21-27. [Google Scholar] [CrossRef] 
[4] Aoi, W. and Marunaka, Y. (2014) Importance of pH Homeostasis in Metabolic Health and Diseases: Crucial Role of Membrane Proton Transport. BioMed Research International, 2014, Article ID: 598986. [Google Scholar] [CrossRef] [PubMed]
[5] Swietach, P. (2019) What Is pH Regulation, and Why Do Cancer Cells Need It? Cancer and Metastasis Reviews, 38, 5-15. [Google Scholar] [CrossRef] [PubMed]
[6] Elsaesser, T. and Schmetzer, B. (1987) Excited-State Proton Transfer in 2-(2'-Hydroxyphenyl)benzothiazole: Formation of the Anion in Polar Solvents. Chemical Physics Letters, 140, 293-299. [Google Scholar] [CrossRef] 
[7] Sinha, H.K. and Dogra, S.K. (1986) Ground and Excited State Prototropic Reactions in 2-(o-Hydroxyphenyl)benzi- midazole. Chemical Physics, 102, 337-347. [Google Scholar] [CrossRef] 
[8] Saroj, M.K., Payal, R., Jain, S.K., et al. (2020) Study of Prototropic Reactions of Indole Chalcone Derivatives in Ground and Excited States Using Absorption and Fluorescence Spectroscopy. Journal of Molecular Liquids, 302, 112164. [Google Scholar] [CrossRef] 
[9] Lewandowska, A., Wróblewski, D., Guzow, K., et al. (2018) Acid-Base Properties of 3-[2-(n-quinolinyl) Benzoxazol-5-yl]alanine Derivatives in the Ground and Excited State. Experimental and Theoretical Studies. Journal of Photochemistry and Photobiology A: Chemistry, 353, 191-199. [Google Scholar] [CrossRef] 
[10] Zhang, Y., Zhang, W., Bian, Y., et al. (2022) Tuning Luminescence of the Fluorescent Molecule 2-(2-Hydroxyphenyl)- 1H-Benzimidazole via Zeolitic Imidazolate Framework-8. RSC Advances, 12, 9342-9350. [Google Scholar] [CrossRef] 
[11] Sahu, S., Das, M. and Krishnamoorthy, G. (2016) Switching between cis and trans Anions of 2-(2'-Hydroxy- phenyl)benzimidazole: A Molecular Rotation Perturbed by Chemical Stabilization. Physical Chemistry Chemical Physics, 18, 11081-11090. [Google Scholar] [CrossRef] 
[12] Behera, S.K., Sadhuragiri, G., Elumalai, P., et al. (2016) Exclusive Excited State Intramolecular Proton Transfer from a 2-(2'-Hydroxyphenyl)benzimidazole Derivative. RSC Advances, 6, 59708-59717. [Google Scholar] [CrossRef] 
[13] Das, M., Brahma, M. and Krishnamoorthy, G. (2021) Controlling the Photoswitching of 2-(4'-Diethylamino- 2'-hydroxyphenyl)-1H-imidazo-[4,5-b] Pyridine by pH. Journal of Photochemistry and Photobiology A: Chemistry, 421, 113504. [Google Scholar] [CrossRef] 
[14] Behera, S.K. and Krishnamoorthy, G. (2015) Relay Proton Transfer Triggered Twisted Intramolecular Charge Transfer. Photochemical & Photobiological Sciences, 14, 2225-2237. [Google Scholar] [CrossRef] 
[15] Mishra, A. and Krishnamoorthy, G. (2012) Photophysical Study of 2-(4'-N,N-Dimethylaminophenyl)oxazolo [4,5-b] pyridine in Different Solvents and at Various pH. Photochemical & Photobiological Sciences, 11, 1356-1367. [Google Scholar] [CrossRef] [PubMed]
[16] Jones, R.O. and Gunnarsson, O. (1989) The Density Functional Formalism, Its Applications and Prospects. Reviews of Modern Physics, 61, 689. [Google Scholar] [CrossRef] 
[17] Fermi, E. (1928) Eine statistische Methode zur Bestimmung einiger Eigenschaften des Atoms und ihre Anwendung auf die Theorie des periodischen Systems der Elemente. European Physical Journal, 48, 73-79. [Google Scholar] [CrossRef] 
[18] Chen, S.G., Kwok, Y.H. and Chen, G.H. (2018) Time-Dependent Density Functional Theory for Open Systems and Its Applications. Accounts of Chemical Research, 51, 385-393. [Google Scholar] [CrossRef] [PubMed]