Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions
Abstract
:1. Introduction
2. Results and Discussions
2.1. Synthesis of Studied Compounds
2.2. UV-Vis Spectra
2.2.1. Isatin Aryl Hydrazones
2.2.2. ((Arylamino)Methylene)Indolin-2-Ones 4 and 5
2.3. Photochemistry of Studied Compounds
2.3.1. Photoisomerization of Isatin Arylhydrazones
2.3.2. Phototautomerization of Isatin Arylhydrazones
2.3.3. Photoisomerisation of ((Arylamino)Methylene)Indolin-2-Ones 4 and 5
2.3.4. Phototautomerization of ((Arylamino)Methylene)Indolin-2-Ones 4 and 5
2.4. Anions of Studied Compounds
2.5. ON/OFF Switching
2.5.1. ON/OFF Switching of Isatin Arylhydrazones 1–3 and ((Arylamino)Methylene)Indolin-2-Ones 4 and 5
2.5.2. ON/OFF Switching of Anions of Arylhydrazone 1–3 and Compounds 4 and 5
3. Materials and Methods
3.1. General Information
3.2. Synthesis
3.2.1. Synthesis of Hydrazones 1–3
3.2.2. Synthesis of Compounds 5 and 6
3.3. Spectroscopic Measurements
3.4. HPLC Chromatography
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–5 are available from the authors. |
Compound | cZhydrazo × 106 [mol·dm−3] | cEhydrazo × 106 [mol·dm−3] | cZhydrazo/cEhydrazo | cEazo |
---|---|---|---|---|
1 | 7.30 | 2.70 | 2.70 | - |
2Z | 6.64 | 3.36 | 1.98 | - |
3Z | 1.68 | 8.31 | - | 0.20 |
4 | 5.68 | 4.32 | 1.31 | - |
5 | 9.06 | 0.94 | 9.67 | - |
cTBAF [mol·dm−3] | k [s−1] |
---|---|
1 × 10−4 | 0.008 |
2.5 × 10−4 | 0.009 |
5 × 10−4 | 0.025 |
1 × 10−3 | 0.040 |
Compound | CTBAF [mol·dm−3] | kZanion [s−1] | kZanion-Eanion [s−1] |
---|---|---|---|
4 | 1 × 10−2 | / | 0.002 |
5 | 2 × 10−4 | 1.025 | 0.019 |
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Tisovský, P.; Csicsai, K.; Donovalová, J.; Šandrik, R.; Sokolík, R.; Gáplovský, A. Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions. Molecules 2020, 25, 3082. https://doi.org/10.3390/molecules25133082
Tisovský P, Csicsai K, Donovalová J, Šandrik R, Sokolík R, Gáplovský A. Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions. Molecules. 2020; 25(13):3082. https://doi.org/10.3390/molecules25133082
Chicago/Turabian StyleTisovský, Pavol, Klaudia Csicsai, Jana Donovalová, Róbert Šandrik, Róbert Sokolík, and Anton Gáplovský. 2020. "Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions" Molecules 25, no. 13: 3082. https://doi.org/10.3390/molecules25133082