Article
Open Access
Supplementary data
Published/Copyright:
August 1, 2012
Table S1
Total energiesa at B3LYP/6-311++G** and relative energyb in the gas phase and in the solvents.
| R | Tautomer | Gas (1.0) | Benzene (2.2) | THF (7.4) | DMSO (46.7) | Water (78.4) |
|---|---|---|---|---|---|---|
| OH | -864.953 | -864.968 | -864.976 | -864.980 | -864.981 | |
| NO2 | NH | -864.947 | -864.962 | -864.974 | -864.979 | -864.980 |
| E2-E1 | -3.56 | -3.23 | -1.53 | -0.56 | -0.68 | |
| OH | -752.668 | -752.679 | -752.686 | -752.689 | -752.690 | |
| CN | NH | -752.660 | -752.674 | -752.684 | -752.688 | -752.688 |
| E2-E1 | -4.70 | -3.16 | -1.71 | -0.96 | -0.86 | |
| OH | -759.673 | -759.682 | -759.688 | -759.690 | -759.691 | |
| F | NH | -759.668 | -759.679 | -759.687 | -759.691 | -759.691 |
| E2-E1 | -2.92 | -1.61 | -0.323 | 0.28 | 0.38 | |
| OH | -660.410 | -660.419 | -660.424 | -660.427 | -660.427 | |
| H | NH | -660.4038 | -660.414 | -660.422 | -660.425 | -660.426 |
| E2-E1 | -3.98 | -2.16 | -1.35 | -0.79 | -0.83 | |
| OH | -699.743 | -699.751 | -699.757 | -699.759 | -699.759 | |
| CH3 | NH | -699.739 | -699.749 | -699.756 | -699.759 | -699.759 |
| E2-E1 | -2.54 | -1.41 | -0.386 | 0.06 | 0.00 | |
| OH | -715.794 | -715.806 | -715.814 | -715.817 | -715.817 | |
| NH2 | NH | -715.795 | -715.808 | -715.817 | -715.820 | -715.821 |
| E2-E1 | 0.44 | 1.11 | 1.68 | 1.93 | 1.92 |
Table S2
Selected molecular parameters of optimized structure of 3-hydroxy-1,3,5-thiadiazole at B3LYP level of theorya.
| NO2 | CN | F | H | CH3 | NH2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Parameter | OH | NH | OH | NH | OH | NH | OH | NH | OH | NH | OH | NH |
| N2=C3 | 1.31 | – | 1.31 | – | 1.30 | – | 1.31 | – | 1.30 | – | 1.29 | – |
| C4=N5 | 1.30 | 1.29 | 1.32 | 1.30 | 1.28 | 1.27 | 1.30 | 1.29 | 1.31 | 1.29 | 1.31 | 1.30 |
| C3=O6 | – | 1.22 | – | 1.22 | – | 1.22 | – | 1.23 | – | 1.23 | – | 1.23 |
| C3–OH | 1.32 | – | 1.32 | – | 1.33 | – | 1.33 | – | 1.33 | – | 1.33 | – |
| N2–C3 | – | 1.38 | – | 1.37 | – | 1.36 | – | 1.37 | – | 1.36 | – | 1.35 |
| N2–H7 | – | 1.03 | – | 1.03 | – | 1.03 | – | 1.03 | – | 1.03 | – | 1.03 |
| O6–H7 | 0.99 | – | 0.99 | – | 0.99 | – | 0.99 | – | 0.98 | – | 0.99 | – |
Table 3
Table S3 Calculated dipole moments of optimized tautomers (Debye).
| R | Tautomer | Gas (1.0)a | Benzene (2.2)a | THF (7.4)a | DMSO (46.7)a | Water (78.4)a |
|---|---|---|---|---|---|---|
| NO2 | OH | 4.04 | 5.5372 | 6.2827 | 6.6163 | 6.6857 |
| NH | 6.32 | 8.2959 | 9.8838 | 10.5856 | 10.6697 | |
| CN | OH | 4.29 | 5.1154 | 5.7592 | 6.0325 | 6.0567 |
| NH | 6.56 | 8.1454 | 9.4658 | 10.0485 | 10.1168 | |
| F | OH | 2.1727 | 2.6264 | 2.9787 | 3.1312 | 3.1413 |
| NH | 4.2119 | 5.2568 | 6.1131 | 6.4946 | 6.5309 | |
| H | OH | 1.3777 | 1.7750 | 2.1022 | 2.2428 | 2.2538 |
| NH | 2.8109 | 3.5824 | 4.2368 | 4.5330 | 4.5650 | |
| CH3 | OH | 1.6665 | 2.0973 | 2.4623 | 2.6250 | 2.6344 |
| NH | 2.0158 | 2.7349 | 3.3552 | 3.6375 | 3.6707 | |
| NH2 | OH | 2.57 | 3.2438 | 3.8212 | 4.0842 | 4.1039 |
| NH | 1.10 | 1.4344 | 1.7682 | 1.9318 | 1.9527 |
aRelative dielectric constant in parentheses.
Table S4
Calculated NBO charges on ring atoms of 3-hydroxy-1,3,5-thiadiazole.
| ɛ= | (1.0) | (2.2) | (7.4) | (46.7) | (78.4) | (1.0) | (2.2) | (7.4) | (46.7) | (78.4) | |
|---|---|---|---|---|---|---|---|---|---|---|---|
| R | Atom | OH form | NH form | ||||||||
| S1 | 0.810 | 0.882 | 0.906 | 0.916 | 0.918 | 0.758 | 0.837 | 0.901 | 0.927 | 0.930 | |
| N2 | -0.643 | -0.669 | -0.674 | -0.675 | -0.675 | -0.769 | -0.766 | -0.759 | -0.755 | -0.754 | |
| NO2 | C3 | 0.466 | 0.492 | 0.500 | 0.504 | 0.505 | 0.582 | 0.591 | 0.595 | 0.596 | 0.596 |
| C4 | 0.239 | 0.217 | 0.219 | 0.219 | 0.220 | 0.254 | 0.236 | 0.226 | 0.222 | 0.223 | |
| N5 | -0.550 | -0.551 | -0.562 | -0.567 | -0.569 | -0.527 | -0.528 | -0.536 | -0.542 | -0.543 | |
| S1 | 0.833 | 0.857 | 0.873 | 0.881 | 0.883 | 0.783 | 0.826 | 0.866 | 0.885 | 0.887 | |
| N2 | -0.657 | -0.667 | -0.672 | -0.674 | -0.673 | -0.776 | -0.766 | -0.757 | -0.753 | -0.752 | |
| CN | C3 | 0.505 | 0.515 | 0.523 | 0.526 | 0.527 | 0.610 | 0.615 | 0.616 | 0.617 | 0.617 |
| C4 | -0.008 | -0.011 | -0.015 | -0.017 | -0.023 | 0.009 | 0.002 | -0.007 | -0.012 | -0.012 | |
| N5 | -0.530 | -0.543 | -0.553 | -0.557 | -0.557 | -0.507 | -0.518 | -0.527 | -0.530 | -0.530 | |
| S1 | 0.771 | 0.779 | 0.784 | 0.789 | 0.789 | 0.720 | 0.746 | 0.770 | 0.782 | 0.783 | |
| N2 | -0.603 | -0.661 | -0.631 | -0.633 | -0.634 | -0.768 | -0.756 | -0.747 | -0.743 | -0.743 | |
| F | C3 | 0.527 | 0.434 | 0.535 | 0.528 | 0.528 | 0.545 | 0.584 | 0.548 | 0.547 | 0.548 |
| C4 | 0.424 | 0.532 | 0.440 | 0.444 | 0.444 | 0.536 | 0.539 | 0.538 | 0.537 | 0.537 | |
| N5 | -0.650 | -0.659 | -0.667 | -0.668 | -0.668 | -0.587 | -0.600 | -0.609 | -0.613 | -0.613 | |
| S1 | 0.769 | 0.773 | 0.773 | 0.772 | 0.772 | 0.710 | 0.773 | 0.755 | 0.765 | 0.766 | |
| N2 | -0.567 | -0.588 | -0.602 | -0.608 | -0.609 | -0.778 | -0.768 | -0.761 | -0.757 | -0.757 | |
| H | C3 | -0.039 | -0.037 | -0.035 | -0.034 | -0.034 | 0.573 | 0.574 | 0.573 | 0.572 | 0.573 |
| C4 | 0.459 | 0.466 | 0.471 | 0.473 | 0.473 | -0.011 | -0.013 | -0.017 | -0.019 | -0.019 | |
| N5 | -0.667 | -0.681 | -0.690 | -0.693 | -0.693 | -0.542 | -0.562 | -0.575 | -0.581 | -0.581 | |
| S1 | 0.752 | 0.756 | 0.754 | 0.752 | 0.752 | 0.695 | 0.716 | 0.735 | 0.744 | 0.745 | |
| N2 | -0.664 | -0.678 | -0.687 | -0.690 | -0.690 | -0.770 | -0.762 | -0.755 | -0.752 | -0.751 | |
| CH3 | C3 | 0.467 | 0.476 | 0.482 | 0.485 | 0.486 | 0.582 | 0.584 | 0.584 | 0.584 | 0.584 |
| C4 | 0.142 | 0.141 | 0.145 | 0.184 | 0.148 | 0.160 | 0.163 | 0.163 | 0.162 | 0.163 | |
| N5 | -0.583 | -0.600 | -0.613 | -0.618 | -0.619 | -0.562 | -0.579 | -0.591 | -0.596 | -0.596 | |
| S1 | 0.731 | 0.721 | 0.711 | 0.705 | 0.705 | 0.668 | 0.667 | 0.686 | 0.690 | 0.691 | |
| N2 | -0.651 | -0.667 | -0.685 | -0.689 | -0.689 | -0.757 | -0.752 | -0.747 | -0.745 | -0.744 | |
| NH2 | C3 | 0.446 | 0.457 | 0.472 | 0.475 | 0.476 | 0.582 | 0.583 | 0.584 | 0.584 | 0.584 |
| C4 | 0.306 | 0.313 | 0.319 | 0.321 | 0.322 | 0.319 | 0.324 | 0.327 | 0.327 | 0.328 | |
| N5 | -0.648 | -0.673 | -0.690 | -0.698 | -0.699 | -0.647 | -0.672 | -0.688 | -0.694 | -0.695 |
Table S5
Selected frequencies (in cm-1) of tautomers at B3LYP/6-311++G** level of theory in the gas phase.
| NO2 | CN | F | H | CH3 | NH2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Bond | OH | NH | OH | NH | OH | NH | OH | NH | OH | NH | OH | NH |
| N2–H7 | – | 3618.79 | – | 3620.26 | – | 3624.33 | – | 3629.97 | – | 3628.68 | – | 3632.22 |
| O6–H7 | 3797.26 | – | 3794.31 | – | 3797.4 | – | 3799.2 | – | 3799.58 | – | 3802.14 | – |
| N2=C3 | 1595.27 | – | 1571 | – | 1605.42 | – | 1578 | – | 1596.65 | – | 1606 | – |
| C3=O6 | – | 1788.27 | – | 1782.31 | – | 1784.14 | – | 1760.42 | – | 1750.69 | – | 1752.57 |
| C4=N5 | – | 1590.26 | – | 1530.93 | – | 1629.8 | – | 1558.25 | – | 1600.06 | – | 1592 |
Published Online: 2012-08-01
Published in Print: 2012-08-01
©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston
This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Creative Commons
BY-NC-ND 3.0
Articles in the same Issue
- Supplementary data
- Masthead
- Masthead
- Preliminary Communications
- Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
- Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
- Research Articles
- Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
- Efficient synthesis of selected phthalazine derivatives
- Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
- Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
- Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
- Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
- Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
- One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
- Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects
