UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base
Abstract
:1. Introduction
2. Experimental and Computational Methods
2.1. Synthesis Procedure and Characterization
2.2. Matrix-Isolation and UV-Irradiation Experiments
2.3. Quantum Chemical Calculations
3. Results and Discussion
3.1. Geometrical Features and Energies of BBAP Isomeric Structures
3.2. Infrared Spectrum of Matrix-Isolated BBAP
3.3. Narrowband UV-Induced Rotamerization of Phenyl Ring
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Conformer | ΔEel | ΔE(0) | ΔG298.15 | P298.15 (%) |
---|---|---|---|---|
I | 0.00 | 0.00 | 0.00 | 89 |
II | 3.52 | 3.91 | 6.83 | 6 |
III | 3.65 | 4.16 | 7.13 | 5 |
IV | 13.29 | 13.01 | 14.63 | |
V | 15.23 | 14.58 | 14.09 | |
VI | 12.83 | 12.23 | 14.09 | |
VII | 14.37 | 14.14 | 16.80 | |
VIII | 21.64 | 21.17 | 25.05 | |
IX | 21.88 | 20.57 | 24.27 | |
X | 22.09 | 20.76 | 22.50 | |
XI | 28.74 | 27.18 | 27.92 |
C–N=C–C | H–O–C–CN | CH–C–N=C | N=C–C–CH | CH–C–O–C | C–O–CH2–C | O–CH2–C–C | |
---|---|---|---|---|---|---|---|
Conformer | α | β | γ | δ | ε | ζ | |
I | –177.4 | –2.7 | 21.7 | 6.7 | –0.7 | –179.5 | 80.1/–98.9 |
II | –177.0 | –3.1 | 23.4 | 8.3 | 5.6 | –78.7 | –31.5/151.4 |
III | –177.5 | –2.9 | 22.4 | 4.9 | –6.7 | 79.3 | 29.5/–153.3 |
IV | –176.4 | –3.2 | 22.8 | 13.6 | –95.8 | 74.2 | 68.6/–111.2 |
V | –179.1 | –2.3 | 16.4 | –3.0 | 87.0 | –77.8 | –64.6/115.5 |
VI | –179.3 | –3.2 | 16.2 | 179.3 | –0.3 | –179.3 | –84.2/95.1 |
VII | –179.2 | –1.5 | 12.4 | 177.1 | 2.4 | –77.6 | –30.8/152.1 |
VIII | 179.9 | –1.7 | 25.9 | –175.3 | –105.4 | 74.2 | 68.7/–111.0 |
IX | –179.4 | –3.9 | 28.1 | 179.5 | –98.5 | 174.9 | –27.3/154.7 |
X | –179.7 | –3.2 | 29.7 | –177.1 | –100.1 | 170.5 | –67.4/112.8 |
XI | –177.9 | –2.1 | 30.9 | –152.6 | 72.2 | –169.4 | 88.6/–90.4 |
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Sıdır, İ.; Gülseven Sıdır, Y.; Góbi, S.; Berber, H.; Fausto, R. UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base. Photochem 2022, 2, 376-389. https://doi.org/10.3390/photochem2020026
Sıdır İ, Gülseven Sıdır Y, Góbi S, Berber H, Fausto R. UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base. Photochem. 2022; 2(2):376-389. https://doi.org/10.3390/photochem2020026
Chicago/Turabian StyleSıdır, İsa, Yadigar Gülseven Sıdır, Sándor Góbi, Halil Berber, and Rui Fausto. 2022. "UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base" Photochem 2, no. 2: 376-389. https://doi.org/10.3390/photochem2020026