Complexes of Hydrogen Peroxide, the Simplest Chiral Molecule, with L- and D-Serine Enantiomers and Their Clusters: MP2 and DFT Calculations †
Abstract
:1. Introduction
2. Results and Discussion
2.1. M-P Transition Energies of Hydrogen Peroxide in the Gas Phase and in Aqueous Solution
2.2. Clusters of Serine Molecules
2.3. Interaction of M- and P-Hydrogen Peroxide with L- and D-Serine Enantiomers
2.4. Complexes of Two Serine Molecules and Their Complexes with Two Hydrogen Peroxide Molecules, DFT Calculation Method ωb97xd/6-311+G**
2.5. Complexes of Four Serine Molecules with a Hydrogen Peroxide Molecule in the Gas Phase
2.6. Complexes of Four Serine Molecules with a Hydrogen Peroxide Molecule in an Aqueous Solution
3. Calculation Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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n | E, a.u. | μ, D | HOMO, a.u. | LUMO, a.u. |
---|---|---|---|---|
1 | −398.8337836 | 4.1518 | −0.34101 | 0.08516 |
2 | −797.6798965 | 2.4455 | −0.33131 | 0.09125 |
3 | −1196.5696345 | 2.9664 | −0.31891 | 0.10479 |
4 | −1595.427764 | 7.0445 | −0.31052 | 0.10190 |
6 | −2393.1876883 | 6.1978 | −0.31462 | 0.08978 |
8 | −3190.9895845 | 8.0066 | −0.31578 | 0.08057 |
10 | −3988.7061529 | 7.5975 | −0.31582 | 0.06749 |
12 | −4786.4338597 | 8.0780 | −0.32131 | 0.06596 |
14 | −5584.1619728 | 4.9998 | −0.31480 | 0.06980 |
16 | −6381.8954629 | 5.9206 | −0.31508 | 0.07181 |
No | Complex | E(MP2), a.u. | HOMO, a.u. | LUMO, a.u. |
---|---|---|---|---|
1 | L-Ser-M-H2O2 | −549.2293614 | −0.43598 | 0.02014 |
2 | D-Ser-M-H2O2 | −549.2267844 | −0.44553 | 0.02009 |
3 | L-Ser-P-H2O2 | −549.2320886 | −0.42693 | 0.02577 |
4 | D-Ser-P-H2O2 | −549.2283007 | −0.43766 | 0.02749 |
5 | L-Ser-M-H2O2/H2O | −549.2726099 | −0.43096 | 0.03994 |
6 | D-Ser-M-H2O2/H2O | −549.269142 | −0.43224 | 0.04013 |
7 | L-Ser-P-H2O2/H2O | −549.2729312 | −0.43227 | 0.04068 |
8 | D-Ser-P-H2O2/H2O | −549.2694565 | −0.43404 | 0.04029 |
No | Complex | ΔE(MP2), kcal/mol |
---|---|---|
1 | L-Ser-M-H2O2 | −10.43 |
2 | D-Ser-M-H2O2 | −8.81 |
3 | L-Ser-P-H2O2 | −12.14 |
4 | D-Ser-P-H2O2 | −9.76 |
5 | L-Ser-M-H2O2/H2O | −10.91 |
6 | D-Ser-M-H2O2/H2O | −8.73 |
7 | L-Ser-P-H2O2/H2O | −11.11 |
8 | D-Ser-P-H2O2/H2O | −8.93 |
Complex | Dihedral HOOH Angles | E, a.u. | HOMO, a.u. | LUMO, a.u. | ΔE, kcal/mol |
---|---|---|---|---|---|
2 L-Ser_2 H2O2(MM) | −89.686 −92.237 | −1101.187021 | −0.35710 | 0.06506 | −33.15 |
2 D-Ser_2 H2O2(MM) | −89.066 −97.170 | −1101.1754803 | −0.34637 | 0.06636 | −29.24 |
2 L-Ser | − | −798.0269538 | −0.35346 | 0.06376 | −18.14 (2H2O2 MM) |
2 D-Ser | − | −798.0207126 | −0.34609 | 0.06404 | −14.82 (2H2O2 MM) |
L-Ser or D-Ser | − | −398.9870594 | −0.34896 | 0.06487 | − |
H2O2 | −97.079 | −151.5655781 | −0.39364 | 0.08984 | − |
Complex | Dihedral HOOH Angle | E, a.u. | HOMO, a.u. | LUMO, a.u. |
---|---|---|---|---|
4 L-Ser_M-H2O2 | −88.04 | −1747.54748 | −0.33028 | 0.04021 |
4 L-Ser_P-H2O2 | 114.29 | −1747.54683 | −0.32850 | 0.03422 |
4 D-Ser_M-H2O2 | −162.15 | −1747.55344 | −0.34232 | 0.04288 |
4 D-Ser_P-H2O2 | 133.38 | −1747.54856 | −0.33931 | 0.04293 |
4 L-Ser | − | −1595.96141 | −0.32207 | 0.04472 |
4 D-Ser | − | −1595.97878 | −0.33906 | 0.03984 |
H2O2 | −119.09 | −151.54948 | −0.37504 | 0.08309 |
Complex | ΔE, kcal/mol, Gas Phase | ΔE, kcal/mol, Aqueous Solution |
---|---|---|
4 L-Ser_M-H2O2 | −22.96 | −12.89 |
4 L-Ser_P-H2O2 | −22.55 | −15.01 |
4 D-Ser_M-H2O2 | −15.74 | −8.25 |
4 D-Ser_P-H2O2 | −12.74 | −6.51 |
Complex | Dihedral HOOH Angle | E, a.u. | HOMO, a.u. | LUMO, a.u. |
---|---|---|---|---|
4 L-Ser_M_H2O2 | −83.153 | −1747.6606928 | −0.34978 | 0.06214 |
4 L-Ser_P_H2O2 | 109.769 | −1747.66408063 | −0.34937 | 0.06173 |
4 D-Ser_M_H2O2 | −164.026 | −1747.6584351 | −0.34528 | 0.06505 |
4 D-Ser_P_H2O2 | 119.169 | −1747.655658 | −0.35018 | 0.06481 |
4 L-Ser | − | −1596.074579 | −0.34844 | 0.06130 |
4 D-Ser | − | −1596.079713 | −0.35189 | 0.06226 |
H2O2 | −97.079 | −151.5655781 | −0.39364 | 0.08984 |
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Borisov, Y.A.; Kiselev, S.S.; Budnik, M.I.; Snegur, L.V. Complexes of Hydrogen Peroxide, the Simplest Chiral Molecule, with L- and D-Serine Enantiomers and Their Clusters: MP2 and DFT Calculations. Molecules 2024, 29, 3955. https://doi.org/10.3390/molecules29163955
Borisov YA, Kiselev SS, Budnik MI, Snegur LV. Complexes of Hydrogen Peroxide, the Simplest Chiral Molecule, with L- and D-Serine Enantiomers and Their Clusters: MP2 and DFT Calculations. Molecules. 2024; 29(16):3955. https://doi.org/10.3390/molecules29163955
Chicago/Turabian StyleBorisov, Yurii A., Sergey S. Kiselev, Mikhail I. Budnik, and Lubov V. Snegur. 2024. "Complexes of Hydrogen Peroxide, the Simplest Chiral Molecule, with L- and D-Serine Enantiomers and Their Clusters: MP2 and DFT Calculations" Molecules 29, no. 16: 3955. https://doi.org/10.3390/molecules29163955