Structural Relevance of Intramolecular H-Bonding in Ortho-Hydroxyaryl Schiff Bases: The Case of 3-(5-bromo-2-hydroxybenzylideneamino) Phenol
Abstract
:1. Introduction
2. Experimental Procedures and Computational Methods
2.1. Synthesis
2.2. Matrix-Isolation Experiments
2.3. Theoretical Calculations
3. Results and Discussion
3.1. Structures and Conformational Landscapes of BHAP Isomeric Forms
3.2. Natural Bond Orbital Analysis
3.3. Infrared Spectrum of BHAP in an Ar Matrix
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Dihedral Angles | |||||
---|---|---|---|---|---|
Conformer | C–C=N–C | C–C–O–H α | C–C–N=C β | C–C–C=N ϒ | C–C–O–H δ |
E-enol-imine | |||||
I | −177.2 | 0.3 | 37.8 | 0.7 | −0.3 |
II | −177.3 | 178.6 | 36.9 | 0.6 | −0.3 |
III | −177.4 | 0.5 | 43.5 | 4.4 | 179.3 |
IV | −177.4 | 179.1 | 43.2 | 4.3 | 179.1 |
V | −177.1 | 0.2 | −144.5 | 0.6 | −0.1 |
VI | −177.1 | −179.1 | −143.6 | 0.6 | −0.3 |
VII | −177.0 | 0.2 | −140.9 | 2.7 | 178.7 |
VIII | −177.2 | −178.3 | −139.2 | 2.5 | 179.4 |
IX | −175.6 | 1.6 | 42.0 | −171.4 | 9.4 |
X | −176.2 | 178.9 | 40.6 | −173.4 | 5.6 |
XI | −177.3 | 0.2 | 39.6 | −178.5 | 178.7 |
XII | −177.3 | 179.2 | 39.6 | −178.4 | 179.8 |
XIII | −175.9 | −0.8 | −141.9 | −172.6 | 6.4 |
XIV | −176.0 | −178.5 | −140.4 | −173.0 | 6.8 |
XV | −177.1 | 0.1 | −144.1 | −178.9 | 179.6 |
XVI | −177.2 | −178.8 | −142.3 | −179.3 | 179.4 |
Z-enol-imine | |||||
I | 7.2 | 0.6 | −128.6 | 38.8 | −23.5 |
II | 6.7 | −179.5 | −126.9 | 39.1 | −21.1 |
III | 5.5 | −1.4 | −133.1 | 47.2 | −175.0 |
IV | 5.7 | −176.3 | −131.9 | 47.1 | −176.5 |
V | 6.1 | −0.5 | 58.2 | 39.5 | −21.9 |
VI | 6.3 | −179.4 | 58.6 | 38.9 | −21.7 |
VII | 5.1 | 0.9 | 52.7 | 47.3 | −175.4 |
VIII | 5.3 | −178.2 | 53.2 | 46.5 | −176.0 |
IX | 7.8 | 0.8 | −127.1 | −148.7 | 8.2 |
X | 7.3 | −179.4 | −124.7 | −148.5 | 7.8 |
XI | 8.1 | 0.5 | −122.9 | −154.6 | −176.9 |
XII | 7.6 | −179.2 | −120.7 | −154.4 | −176.6 |
XIII | 7.2 | −1.5 | 59.3 | −148.4 | 6.6 |
XIV | 7.3 | −178.7 | 60.9 | −148.7 | 9.3 |
XV | 7.3 | −0.2 | 65.2 | −154.5 | −176.0 |
XVI | 7.4 | −179.2 | 64.7 | −153.8 | −177.0 |
Conformer | ΔEel | ΔE(0) | ΔG°298.15 | μ | ΔEel | ΔE(0) | ΔG298.15 |
---|---|---|---|---|---|---|---|
E-enol-imine | |||||||
I | 1.69 | 1.51 | 0.70 | 1.36 | |||
II | 0.10 | 0.15 | −0.51 | 3.35 | |||
III | 56.77 | 54.10 | 51.30 | 2.78 | |||
IV | 55.71 | 53.20 | 50.51 | 1.63 | |||
V | 0.00 | 0.00 | 0.00 | 1.01 | |||
VI | 0.84 | 0.67 | 0.67 | 3.53 | |||
VII | 54.95 | 52.51 | 49.66 | 2.95 | |||
VIII | 56.38 | 53.65 | 50.51 | 0.91 | |||
IX | 47.18 | 44.45 | 41.31 | 2.43 | |||
X | 45.47 | 42.88 | 38.97 | 3.33 | |||
XI | 39.76 | 37.18 | 34.54 | 4.57 | |||
XII | 38.89 | 36.58 | 34.25 | 3.20 | |||
XIII | 44.90 | 42.38 | 39.57 | 1.83 | |||
XIV | 46.28 | 43.51 | 40.72 | 3.88 | |||
XV | 38.13 | 35.68 | 32.73 | 3.89 | |||
XVI | 39.62 | 36.86 | 33.64 | 4.33 | |||
Z-enol-imine | |||||||
I | 62.99 | 61.92 | 61.52 | 0.80 | 0.25 | 0.29 | 0.46 |
II | 63.25 | 61.94 | 61.44 | 2.72 | 0.51 | 0.31 | 0.37 |
III | 73.30 | 71.33 | 70.23 | 2.93 | 10.56 | 9.70 | 9.16 |
IV | 75.05 | 72.47 | 70.54 | 3.88 | 12.31 | 10.84 | 9.48 |
V | 62.74 | 61.63 | 61.07 | 0.51 | 0.00 | 0.00 | 0.00 |
VI | 63.12 | 61.73 | 60.93 | 2.80 | 0.38 | 0.10 | −0.14 |
VII | 74.60 | 72.25 | 70.38 | 2.96 | 11.86 | 10.62 | 9.31 |
VIII | 75.01 | 72.47 | 70.53 | 3.97 | 12.27 | 10.84 | 9.46 |
IX | 70.42 | 68.65 | 66.04 | 1.66 | 7.68 | 7.02 | 4.98 |
X | 70.67 | 68.82 | 66.26 | 1.82 | 7.93 | 7.19 | 5.20 |
XI | 66.67 | 64.98 | 62.18 | 4.31 | 3.93 | 3.35 | 1.11 |
XII | 67.09 | 65.26 | 62.41 | 3.92 | 4.35 | 3.63 | 1.34 |
XIII | 71.27 | 69.42 | 66.59 | 2.17 | 8.53 | 7.79 | 5.52 |
XIV | 70.42 | 68.58 | 65.80 | 0.72 | 7.68 | 6.95 | 4.73 |
XV | 67.35 | 65.73 | 62.82 | 4.88 | 4.61 | 4.10 | 1.76 |
XVI | 66.87 | 65.14 | 62.33 | 2.89 | 4.13 | 3.51 | 1.26 |
Dihedral Angles | ||||
---|---|---|---|---|
Conformer | C–C=C–N | C–C–O–H α | C–C–N–C β | C–N–C=C ϒ |
keto-amine forms structurally related to the E-enol-imine isomer | ||||
I | 0.0 | 0.0 | 0.0 | 179.9 |
II | 0.0 | −179.9 | −0.7 | 179.9 |
III | 178.4 | 0.6 | 166.5 | 177.5 |
IV | 179.0 | −179.3 | 169.9 | 178.4 |
V | 0.0 | 0.4 | 175.1 | 179.6 |
VI | 0.0 | −179.6 | 174.1 | 179.0 |
VII | 179.1 | 1.6 | −8.7 | 178.6 |
VIII | 178.7 | −179.0 | −9.0 | 178.6 |
keto-amine forms structurally related to the Z-enol-imine isomer | ||||
I | 176.0 | 4.7 | −44.8 | −16.3 |
II | 177.1 | 179.5 | −47.3 | −15.7 |
III | −14.9 | −3.7 | 153.1 | −24.5 |
IV | −15.3 | −176.6 | 156.0 | −23.9 |
V | 177.4 | −1.2 | 131.6 | −15.1 |
VI | 176.6 | −177.9 | 136.9 | −16.1 |
VII | −15.6 | 8.8 | −25.6 | −23.3 |
VIII | −15.3 | 178.3 | −28.2 | −24.2 |
Conformer | ΔEel | ΔE(0) | ΔG°298.15 | μ | ΔEel | ΔE(0) | ΔG298.15 | |
---|---|---|---|---|---|---|---|---|
keto-amine forms structurally related to the E-enol-imine isomer | ||||||||
I | 19.69 | 18.94 | 16.35 | 3.49 | 2.75 | 2.66 | 2.39 | |
II | 16.95 | 16.28 | 13.96 | 5.30 | 0.00 | 0.00 | 0.00 | |
III | 61.49 | 61.03 | 56.80 | 4.74 | 2.95 | 2.86 | 3.82 | |
IV | 58.54 | 58.17 | 52.98 | 5.67 | 0.00 | 0.00 | 0.00 | |
V | 17.87 | 17.01 | 11.28 | 2.97 | 0.92 | 0.72 | –2.68 | |
VI | 18.42 | 17.67 | 14.20 | 5.67 | 1.48 | 1.39 | 0.25 | |
VII | 58.66 | 58.14 | 52.81 | 3.82 | 0.12 | –0.03 | –0.17 | |
VIII | 59.08 | 58.45 | 52.93 | 6.41 | 0.54 | 0.28 | –0.05 | |
keto-amine forms structurally related to the Z-enol-imine isomer | ||||||||
I | 80.86 | 81.47 | 78.49 | 4.46 | 63.91 | 65.19 | 64.53 | |
II | 82.00 | 82.43 | 79.19 | 6.89 | 65.05 | 66.15 | 65.23 | |
III | 94.97 | 94.96 | 93.91 | 4.53 | 36.43 | 36.79 | 40.93 | |
IV | 92.80 | 92.95 | 92.27 | 4.05 | 34.26 | 34.78 | 39.29 | |
V | 82.94 | 83.08 | 79.48 | 5.39 | 65.99 | 66.80 | 65.52 | |
VI | 81.05 | 81.44 | 78.61 | 6.29 | 64.09 | 65.16 | 64.66 | |
VII | 91.88 | 92.47 | 92.00 | 3.91 | 33.34 | 34.30 | 39.02 | |
VIII | 93.01 | 93.29 | 92.87 | 4.75 | 34.47 | 35.12 | 39.89 |
Atom | NBO Charge | Atom | NBO Charge | |
---|---|---|---|---|
C1 | 0.325 | O15 | −0.677 | |
C2 | −0.253 | Br16 | 0.061 | |
C3 | −0.171 | O17 | −0.670 | |
C4 | −0.256 | H18 | 0.220 | |
C5 | 0.154 | H19 | 0.207 | |
C6 | −0.278 | H20 | 0.209 | |
N7 | −0.522 | H21 | 0.209 | |
C8 | 0.162 | H22 | 0.170 | |
C9 | −0.176 | H23 | 0.219 | |
C10 | −0.175 | H24 | 0.223 | |
C11 | −0.138 | H25 | 0.224 | |
C12 | −0.182 | H26 | 0.507 | |
C13 | −0.238 | H27 | 0.468 | |
C14 | 0.376 |
Coefficients (%) b | ||||
---|---|---|---|---|
Orbital | Occupancy (e) a | A | B | Description |
σ(C1–C2) | 1.97297 | 50.75 | 49.25 | C1 sp1.68 + C2 sp1.92 |
π(C1–C2) | 1.68279 | 49.24 | 50.76 | C1 sp3.35 + C2 p |
σ(C1–C6) | 1.97708 | 50.10 | 49.90 | C1 sp1.60 + C6 sp1.85 |
σ(C1–O17) | 1.99029 | 11.14 | 88.86 | C1 p + O17 p |
σ(C2–C3) | 1.90762 | 49.96 | 50.04 | C2 sp1.89 + C3 sp1.79 |
σ(C2–H18) | 1.92993 | 60.78 | 39.22 | C2 sp2.24 + H18 s |
σ(C3–C4) | 1.97617 | 49.69 | 50.31 | C3 sp1.78 + C4 sp1.77 |
π(C3–C4) | 1.68051 | 46.96 | 53.04 | C3 p + C4 p |
σ(C3–H19) | 1.97978 | 60.44 | 39.56 | C3 sp2.54 + H19 s |
σ(C4–C5) | 1.97155 | 49.10 | 50.90 | C4 sp1.87 + C5 sp1.65 |
σ(C4–H20) | 1.97822 | 60.54 | 39.46 | C4 sp2.44 + H20 s |
σ(C5–C6) | 1.96869 | 50.49 | 49.51 | C5 sp1.88 + C6 sp1.78 |
π(C5–C6) | 1.66431 | 46.58 | 53.42 | C5 p + C6 p |
σ(C5–N7) | 1.98468 | 39.31 | 60.69 | C5 sp2.65 + N7 sp1.30 |
σ(C6–H21) | 1.97686 | 60.52 | 39.48 | C6 sp2.45 + H21 s |
σ(N7–C8) | 1.98676 | 59.95 | 40.05 | N7 sp1.33 + C8 sp2.02 |
π(N7–C8) | 1.92978 | 70.93 | 29.07 | N7 p + C8 p |
σ(C8–C9) | 1.97187 | 48.56 | 51.44 | C8 sp1.82 + C9 sp2.11 |
σ(C8–H22) | 1.97565 | 59.42 | 40.58 | C8 sp2.16 + H22 s |
σ(C9–C10) | 1.96315 | 51.13 | 48.87 | C9 sp1.88 + C10 sp1.86 |
π(C9–C10) | 1.64114 | 54.94 | 45.06 | C9 p + C10 p |
σ(C9–C14) | 1.97181 | 51.09 | 48.91 | C9 sp2.02 + C14 sp1.71 |
σ(C10–C11) | 1.97983 | 50.21 | 49.79 | C10 sp1.74 + C11 sp1.55 |
σ(C10–H23) | 1.97719 | 61.05 | 38.95 | C10 sp2.49 + H23 s |
σ(C11–C12) | 1.97972 | 50.32 | 49.68 | C11 sp1.59 + C12 sp1.82 |
π(C11–C12) | 1.64989 | 56.19 | 43.81 | C11 p + C12 p |
σ(C11–Br16) | 1.98466 | 49.53 | 50.47 | C11 sp3.51 + Br16 p |
σ(C12–C13) | 1.96871 | 50.19 | 49.81 | C12 sp1.79 + C13 sp1.74 |
σ(C12–H24) | 1.97873 | 61.21 | 38.79 | C12 sp2.47 + H24 s |
σ(C13–C14) | 1.97688 | 49.33 | 50.67 | C13 sp1.91 + C14 sp1.71 |
π(C13–C14) | 1.58461 | 54.83 | 45.17 | C13 p + C14 p |
σ(C13–H25) | 1.97697 | 61.21 | 38.79 | C13 sp2.43 + H25 s |
σ(C14–O15) | 1.99406 | 33.91 | 66.09 | C14 sp2.86 + O15 sp1.95 |
σ(O15–H26) | 1.98451 | 77.97 | 22.03 | O15 sp2.91 + H26 s |
σ(O17–H27) | 1.98736 | 73.72 | 26.28 | O17 sp3.76 + H27 s |
Lp N7 | 1.60068 | p | ||
Lp1 O15 | 1.97390 | sp1.46 | ||
Lp2 O15 | 1.81108 | p | ||
Lp1 Br16 | 1.99361 | s | ||
Lp2 Br16 | 1.97619 | p | ||
Lp3 Br16 | 1.94629 | p | ||
Lp1 O17 | 1.97920 | sp1.24 | ||
Lp2 O17 | 1.35923 | sp2.01 |
Bond | BO | Bond | BO | Bond | BO | Bond | BO |
---|---|---|---|---|---|---|---|
C1–C2 | 1.35 | O17–H27 | 0.77 | C8–C9 | 1.14 | C14–C9 | 1.27 |
C2–C3 | 1.45 | C2–H18 | 0.92 | C8–H22 | 0.92 | C14–O15 | 1.11 |
C3–C4 | 1.43 | C3–H19 | 0.92 | C9–C10 | 1.33 | O15–H26 | 0.64 |
C4–C5 | 1.36 | C4–H20 | 0.92 | C10–C11 | 1.45 | C10–H23 | 0.92 |
C5–C6 | 1.36 | C6–H21 | 0.92 | C11–C12 | 1.35 | C11–Br16 | 1.03 |
C6–C1 | 1.39 | C5–N7 | 1.07 | C12–C13 | 1.47 | C12–H24 | 0.92 |
C1–O17 | 1.02 | N7–C8 | 1.70 | C13–C14 | 1.34 | C13–H25 | 0.92 |
Exp. | Calculated | Calculated | ||||
---|---|---|---|---|---|---|
Ar Matrix b | V | Approximate Description c | II | Approximate Descriptionc | ||
ν | ν | IIR | ν | IIR | ||
3642/3640 | 3622.9 | 66.48 | νOHp | 3625.1 | 84.3 | νOHp |
3573–3035 | 3033.1 | 536.05 | νOHbp | 3033.6 | 538.1 | νOHbp |
3021 | 3027.7 | 2.81 | νCHbp | 3028.4 | 4.2 | νCHbp |
3025.6 | 11.12 | νCHp | 3023.9 | 5.0 | νCHp | |
3015.9 | 4.44 | νCHp | 3019.4 | 2.0 | νCHp | |
3014.4 | 4.46 | νCHbp | 3014.8 | 4.0 | νCHbp | |
3005 | 3008.2 | 1.29 | νCHbp | 3009.9 | 1.4 | νCHbp |
2993/3005 | 2998.2 | 8.52 | νCHp | 3005.8 | 17.9 | νCHp |
2987/2975 | 2991.1 | 7.78 | νCHp | 2983.9 | 10.3 | νCHp |
2864/2846 | 2878.3 | 34.13 | νCHam | 2877.4 | 34.5 | νCHam |
1630/1626 | 1656.5 | 97.93 | νN=C; νCCam; δCHam | 1658.1 | 117.5 | νN=C; νCCam; δCHam |
1613 | 1644.6 | 23.95 | νCCbp; δOHbp | 1644.7 | 14.5 | νCCbp; δOHbp |
1602/1600 | 1623.9 | 272.72 | νCCp | 1627.3 | 245.1 | νCCp |
1617.6 | 80.99 | νCCp; δOHp | 1612.2 | 114.3 | νCCp; δOHp | |
1593 | 1588.5 | 173.04 | δOHbp; νCCbp; δCHbp; νN=C | 1589.0 | 141.4 | δOHbp; νCCbp; δCHbp; νN=C |
1521/1500 | 1514.8 | 63.04 | νCCp; δCHp; δOHp | 1507.4 | 87.0 | νCCp; δCHp; δOHp |
1495 | 1496.9 | 81.64 | δCHbp; δOHbp; νCCbp | 1494.6 | 156.1 | δCHbp; δOHbp; νCCbp |
1477 | 1478.2 | 87.27 | δCHp-bp; νCCp-bp; δOHp-bp | 1485.5 | 10.7 | δCHp-bp; νCCp-bp; δOHp-bp |
1461 | 1464.1 | 52.23 | νCCbp; δCHbp; δOHbp | 1469.6 | 15.5 | νCCbp; δCHbp; δOHbp |
1421 | 1418.2 | 25.92 | νCCbp; δCHbp; δOHbp; δCHam | 1419.1 | 31.2 | νCCbp; δCHbp; δOHbp; δCHam |
1368/1358 | 1371.9 | 40.64 | δCHam | 1373.8 | 34.5 | δCHam |
1339 | 1338.8 | 2.96 | δCHp; νCCp | 1338.8 | 16.5 | δCHp; νCCp |
1331/1326 | 1334.8 | 2.83 | νCCbp; δCHbp | 1334.9 | 5.0 | νCCbp; δCHbp |
1326.2 | 1.70 | δCCp; δCHp; δOHp | 1318.7 | 92.2 | δCCp; δCHp; δOHp | |
1314 | 1302.9 | 131.61 | νCObp; δCCbp; δCHbp | 1304.2 | 79.5 | νCObp; δCCbp; δCHbp |
1308/1285 | 1292.9 | 28.68 | νCOp; νC-N; δCCp; δCHp | 1282.7 | 47.5 | νCOp; νC-N; δCCp; δCHp |
1264 | 1249.7 | 9.74 | δCHbp | 1250.8 | 17.9 | δCHbp |
1224/1217 | 1215.4 | 56.05 | νCCam; δCHp-bp | 1215.4 | 57.5 | νCCam; δCHp-bp |
1196/1181 | 1186.9 | 169.23 | δOHp; δCHp | 1194.6 | 41.4 | δOHp; δCHp |
1166 | 1178.0 | 28.77 | δCHp; δOHp | 1175.7 | 36.2 | δCHp; δOHp |
1158 | 1158.5 | 160.77 | δCHp; νCp-N; νCOp | 1156.5 | 192.3 | δCHp; νCp-N; νCOp |
1147 | 1144.6 | 7.08 | δCHbp | 1144.6 | 8.9 | δCHbp |
1093 | 1095.7 | 13.00 | δCHp | 1097.4 | 10.8 | δCHp |
1073 | 1084.1 | 15.73 | νC-Br; δCCbp; δCHbp | 1085.2 | 15.9 | νC-Br; δCCbp; δCHbp |
998 | 1005.4 | 7.15 | δCCp; γCHam | 1007.9 | 2.2 | δCCp; γCHam |
994.4 | 10.83 | γCHam | 998.2 | 9.1 | γCHam | |
973 | 973.5 | 0.10 | γCHp | 970.2 | 1.7 | γCHp |
957 | 969.8 | 53.61 | δCCp; δCHp; νCOp | 978.2 | 94.9 | δCCp; δCHp; νCOp |
958.6 | 0.04 | γCHbp | 958.4 | 0.5 | γCHbp | |
897 | 919.5 | 17.42 | δCCbp; δCNC; δCCNam; νCBr | 917.1 | 16.2 | δCCbp; δCNC; δCCNam; νCBr |
875 | 883.7 | 9.64 | γCHp-bp | 884.3 | 17.9 | γCHp-bp |
880.0 | 5.20 | γCHp-bp | 874.1 | 8.2 | γCHp-bp | |
859 | 856.2 | 42.42 | γCCp; γCHp-bp; γOHbp | 866.3 | 12.8 | γCCp; γCHp |
848 | 848.8 | 4.55 | γOHbp | 851.8 | 16.9 | γCHbp; γOHbp |
844 | 827.8 | 83.95 | γCCbp; γCHbp; γOHbp | 828.0 | 80.9 | γCCbp; γCHbp; γOHbp |
824/805 | 813.2 | 7.16 | δCCbp; δCNC; δCCNam | 805.0 | 7.9 | δCCbp; δCNC; δCCNam |
765 | 780.4 | 20.54 | γCHp | 779.0 | 11.8 | γCHp; δCCbp |
758 | 774.9 | 6.42 | γCHp; δCCbp | 775.9 | 34.0 | γCHp |
717 | 729.0 | 1.13 | γCHbp; γCCbp | 728.8 | 1.5 | γCHbp; γCCbp |
685 | 695.7 | 25.80 | γCCp; δCCbp | 694.3 | 22.9 | γCCp; δCCbp |
686.0 | 16.75 | γCCp | 685.2 | 15.2 | γCCp | |
633 | 635.8 | 16.53 | γCCp; δCCbp; γCHp; νCBr | 635.4 | 22.2 | γCCp; δCCbp; γCHp; νCBr |
610 | 624.7 | 8.06 | γCCp; δCCbp; γCHp; νCBr | 623.8 | 5.7 | γCCp; δCCbp; γCHp; νCBr |
571/560 | 574.1 | 10.14 | δCCp-bp; δCNC; δCCNam | 563.8 | 9.9 | δCCp-bp; δCNC; δCCNam |
553 | 552.7 | 4.79 | γCCbp; γCHbp; γCHam | 555.2 | 6.1 | γCCbp; γCHbp; γCHam |
541 | 530.8 | 1.48 | δCCp | 533.7 | 1.3 | δCCp |
528/521 | 516.2 | 17.41 | δCNp | 520.8 | 2.6 | δCNp |
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Sıdır, İ.; Gülseven Sıdır, Y.; Góbi, S.; Berber, H.; Fausto, R. Structural Relevance of Intramolecular H-Bonding in Ortho-Hydroxyaryl Schiff Bases: The Case of 3-(5-bromo-2-hydroxybenzylideneamino) Phenol. Molecules 2021, 26, 2814. https://doi.org/10.3390/molecules26092814
Sıdır İ, Gülseven Sıdır Y, Góbi S, Berber H, Fausto R. Structural Relevance of Intramolecular H-Bonding in Ortho-Hydroxyaryl Schiff Bases: The Case of 3-(5-bromo-2-hydroxybenzylideneamino) Phenol. Molecules. 2021; 26(9):2814. https://doi.org/10.3390/molecules26092814
Chicago/Turabian StyleSıdır, İsa, Yadigar Gülseven Sıdır, Sándor Góbi, Halil Berber, and Rui Fausto. 2021. "Structural Relevance of Intramolecular H-Bonding in Ortho-Hydroxyaryl Schiff Bases: The Case of 3-(5-bromo-2-hydroxybenzylideneamino) Phenol" Molecules 26, no. 9: 2814. https://doi.org/10.3390/molecules26092814