Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach
Abstract
:1. Introduction
2. Methodological Details in Calculations
3. Results and Discussion
3.1. Optimized Structures for Conformers of 1–6 with M06-2X/BSS-A, Together with 7–9
3.2. Structural Feature of 1a–6a and 7–9
3.3. Factors Determining the Relative Energies of 1a–6a
3.4. Contour Plots and Negative Laplacian around the E-∗-E’ Bonds in 1a–6e
3.5. Application of QTAIM-DFA to the E–E’ Bonds in 1a–6e
3.6. Nature of the E–E’ Bonds in 1a–6e
3.7. Factors that Stabilize the E–E’ Bonds and the Conformers
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Species | r(E, E) | φA | Erel | Species | r(E, E) | φA | Erel |
---|---|---|---|---|---|---|---|
(Å) | (°) | (kJ mol−1) | (Å) | (°) | (kJ mol−1) | ||
1a | 2.0736 | −117.4 | 0.0 | 2a | 2.2002 | −85.6 | 0.0 |
1b | 2.0694 | −116.4 | 8.6 | 2b | 2.1963 | −110.1 | 1.0 |
1c | 2.0778 | −119.3 | 14.1 | 2c | 2.1982 | −84.5 | 18.0 |
1d | 2.0561 | 100.3 | 29.3 | 2d | 2.1959 | −78.4 | 23.1 |
1e | 2.2454 | 117.9 | 97.4 | 2e | 2.2079 | −65.0 | 23.7 |
4a | 2.0625 | 67.7 | 0.0 | 5a | 2.1984 | −83.9 | 0.0 |
4b | 2.0471 | −82.2 | 0.3 | 5b | 2.1890 | 84.3 | 15.7 |
4c | 2.0529 | 88.5 | 0.7 | 5c | 2.2011 | 94.0 | 17.5 |
4d | 2.0541 | −75.7 | 3.2 | 5d | 2.2070 | 72.9 | 19.6 |
4e | 2.0515 | 95.7 | 8.8 | 5e | 2.2067 | −66.9 | 27.4 |
7 | 2.0491 | 85.0 | 2 | 8 | 2.1923 | 85.6 | 2 |
3a | 2.3252 | −85.2 | 0.0 | ||||
3b | 2.3215 | −82.5 | 13.6 | ||||
3c | 2.3138 | −92.5 | 34.9 | ||||
3d | 2.3546 | −144.5 | 47.9 | ||||
3e | 2.3320 | 105.2 | 58.8 | ||||
6a | 2.3275 | 88.5 | 0.0 | ||||
6b | 2.3303 | 93.4 | 1.4 | ||||
6c | 2.3309 | 90.2 | 3.3 | ||||
6d | 2.3351 | 74.9 | 3.6 | ||||
6e | 2.3286 | 93.1 | 3.7 | ||||
9 | 2.3236 | 86.1 | 2 |
Compound | ρ(rc) | c∇2ρb(rc) 2 | Hb(rc) | R 3 | θ 4 | kb(rc) 5 | νn 6 | kf 7 | θp:NIV 8 | κp:NIV 9 | Classification/ |
---|---|---|---|---|---|---|---|---|---|---|---|
(Sym: E-∗-E’) | (au) | (au) | (au) | (au) | (°) | (cm−1) | (mdyn Å−1) | (°) | (au−1) | Characterization | |
1a (C1: S-∗-S) | 0.1378 | −0.0106 | −0.0676 | 0.0684 | 188.9 | −2.460 | 493.3 | 0.928 | 197.3 | 0.82 | SS/Covweak |
1b (C1: S-∗-S) | 0.1391 | −0.0113 | −0.0692 | 0.0701 | 189.2 | −2.483 | 513.8 | 1.718 | 197.3 | 0.78 | SS/Covweak |
1c (C1: S-∗-S) | 0.1368 | −0.0103 | −0.0665 | 0.0673 | 188.8 | −2.451 | 489.7 | 0.910 | 197.2 | 0.84 | SS/Covweak |
1d (C1: S-∗-S) | 0.1428 | −0.0124 | −0.0733 | 0.0744 | 189.6 | −2.512 | 506.0 | 0.917 | 197.6 | 0.70 | SS/Covweak |
1e (C1: S-∗-S) | 0.1025 | −0.0011 | −0.0345 | 0.0345 | 181.9 | −2.070 | 353.7 | 0.447 | 193.8 | 3.62 | SS/Covweak |
2a (C1: S-∗-Se) | 0.1169 | −0.0043 | −0.0528 | 0.0530 | 184.7 | −2.195 | 418.7 | 0.545 | 188.1 | 0.23 | SS/Covweak |
2b (C1: S-∗-Se) | 0.1178 | −0.0046 | −0.0535 | 0.0537 | 184.9 | −2.206 | 434.0 | 0.955 | 188.4 | 0.15 | SS/Covweak |
2c (C1: S-∗-Se) | 0.1174 | −0.0045 | −0.0532 | 0.0534 | 184.8 | −2.203 | 421.5 | 0.634 | 188.3 | 0.19 | SS/Covweak |
2d (C1: S-∗-Se) | 0.1176 | −0.0045 | −0.0532 | 0.0534 | 184.8 | −2.203 | 404.6 | 0.684 | 188.7 | 0.21 | SS/Covweak |
2e (C1: S-∗-Se) | 0.1158 | −0.0043 | −0.0520 | 0.0522 | 184.7 | −2.198 | 415.9 | 0.835 | 188.2 | 0.20 | SS/Covweak |
3a (C1: Se-∗-Se) | 0.1027 | −0.0046 | −0.0437 | 0.0440 | 186.0 | −2.265 | 302.0 | 0.346 | 189.0 | 0.83 | SS/Covweak |
3b (C1: Se-∗-Se) | 0.1035 | −0.0048 | −0.0444 | 0.0446 | 186.2 | −2.275 | 310.2 | 0.485 | 189.2 | 0.78 | SS/Covweak |
3c (C1: Se-∗-Se) | 0.1048 | −0.0050 | −0.0458 | 0.0461 | 186.3 | −2.282 | 316.0 | 0.423 | 189.2 | 0.84 | SS/Covweak |
3d (C1: Se-∗-Se) | 0.0988 | −0.0046 | −0.0406 | 0.0409 | 186.4 | −2.291 | 304.2 | 0.684 | 189.8 | 1.31 | SS/Covweak |
3e (C1: Se-∗-Se) | 0.1022 | −0.0045 | −0.0435 | 0.0437 | 185.9 | −2.259 | 300.6 | 0.835 | 189.4 | 0.99 | SS/Covweak |
7 (C2: S-∗-S) | 0.1446 | −0.0131 | −0.0751 | 0.0763 | 189.9 | −2.535 | 513.7 | 2.645 | 197.6 | 0.66 | SS/Covweak |
8 (C1: S-∗-Se) | 0.1189 | −0.0048 | −0.0544 | 0.0547 | 185.0 | −2.213 | 419.7 | 2.072 | 188.6 | 0.38 | SS/Covweak |
9 (C2: Se-∗-Se) | 0.1036 | −0.0050 | −0.0445 | 0.0448 | 186.4 | −2.291 | 307.7 | 2.730 | 189.1 | 0.77 | SS/Covweak |
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Hayashi, S.; Tsubomoto, Y.; Nakanishi, W. Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach. Molecules 2018, 23, 443. https://doi.org/10.3390/molecules23020443
Hayashi S, Tsubomoto Y, Nakanishi W. Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach. Molecules. 2018; 23(2):443. https://doi.org/10.3390/molecules23020443
Chicago/Turabian StyleHayashi, Satoko, Yutaka Tsubomoto, and Waro Nakanishi. 2018. "Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach" Molecules 23, no. 2: 443. https://doi.org/10.3390/molecules23020443