Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Crystallographic Studies
Identification Code | 1 | 2 | 3 | 4 |
---|---|---|---|---|
Empirical formula | C26H19N5O | C23H19N5O | C24H22N6 | C22H17N5O |
Formula weight | 417.46 | 381.43 | 394.48 | 367.41 |
Temperature/K | 296.15 | 296.15 | 296.15 | 296.15 |
Crystal system | monoclinic | monoclinic | triclinic | monoclinic |
Space group | P21/n | P21/c | P-1 | P21/c |
a/Å | 6.5745(2) | 5.9756(18) | 8.8933(10) | 14.9753(17) |
b/Å | 19.9133(6) | 21.573(6) | 11.1477(11) | 6.1220(6) |
c/Å | 15.9805(5) | 14.980(4) | 11.7484(13) | 21.038(2) |
α/° | 90.00 | 90.00 | 91.212(9) | 90.00 |
β/° | 96.369(3) | 93.45(2) | 106.044(10) | 103.992(11) |
γ/° | 90.00 | 90.00 | 108.519(9) | 90.00 |
Volume/Å3 | 2079.25(11) | 1927.7(9) | 1053.8(2) | 1871.6(3) |
Z | 4 | 4 | 2 | 4 |
ρcalcmg/mm3 | 1.334 | 1.314 | 1.243 | 1.304 |
m/mm−1 | 0.677 | 0.084 | 0.077 | 0.084 |
F(000) | 872.0 | 800.0 | 416.0 | 768.0 |
Crystal size/mm3 | 0.48 × 0.16 × 0.15 | 0.48 × 0.08 × 0.05 | 0.32 × 0.26 × 0.17 | 0.43 × 0.15 × 0.05 |
2θ range for data collection | 7.12 to 152° | 5.76 to 58.66° | 5.62 to 58.9° | 5.6 to 59.14° |
Index ranges | −6 ≤ h ≤ 8, | −7 ≤ h ≤ 8, | −11 ≤ h ≤ 9, | −19 ≤ h ≤ 19, |
−25 ≤ k ≤ 21, | −27 ≤ k ≤ 24, | −12 ≤ k ≤ 14, | −8 ≤ k ≤ 7, | |
−20 ≤ l ≤ 19 | −20 ≤ l ≤ 18 | −16 ≤ l ≤ 15 | −29 ≤ l ≤ 26 | |
Reflections collected | 12339 | 11554 | 9379 | 11939 |
Independent reflections | 4304[R(int) = 0.0185] | 4608[R(int) = 0.0727] | 5004[R(int) = 0.0252] | 4597[R(int) = 0.0620] |
Data/restraints/parameters | 4304/0/290 | 4608/1/266 | 5004/0/274 | 4597/1/257 |
Goodness-of-fit on F2 | 1.036 | 1.012 | 1.038 | 0.961 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0428, | R1 = 0.0626, | R1 = 0.0541, | R1 = 0.0601, |
wR2 = 0.1156 | wR2 = 0.0925 | wR2 = 0.1221 | wR2 = 0.1236 | |
Final R indexes [all data] | R1 = 0.0546, | R1 = 0.1988, | R1 = 0.0840, | R1 = 0.1880, |
wR2 = 0.1273 | wR2 = 0.1358 | wR2 = 0.1423 | wR2 = 0.1670 | |
Largest diff. peak/hole/e Å−3 | 0.19/−0.20 | 0.16/−0.19 | 0.25/−0.16 | 0.13/−0.16 |
D | H | A | d(D-H)/Å | d(H-A)/Å | d(D-A)/Å | D-H-A/° |
---|---|---|---|---|---|---|
(1) | ||||||
N4 | H2 | N21 | 0.97 | 1.91 | 2.8750(18) | 171.9 |
(2) | ||||||
C16 | H16 | N32 | 0.93 | 2.58 | 3.496(4) | 168.5 |
N4 | H1 | N22 | 0.893(10) | 2.047(11) | 2.939(3) | 176(3) |
(3) | ||||||
N4 | H1 | N23 | 0.97 | 2.03 | 2.995(2) | 168.8 |
C24 | H24C | N14 | 0.96 | 2.59 | 3.449(3) | 148.7 |
(4) | ||||||
O1 | H1O | N5 | 0.82 | 1.93 | 2.646(3) | 146.1 |
N4 | H2 | N25 | 0.889(10) | 2.033(12) | 2.907(4) | 167(3) |
12 − X, −Y, −Z, 21 − X, 1 − Y, 1 − Z, 3−X, −Y, −Z, 41 + X, +Y, +Z, 5−X, 2 − Y, −Z |
2.3. Geometries Optimization
Bond Lengths (A°) Experimental B3LYP/6-31G (d, p) | ||
O1-C18 | 1.353(2) | 1.430 |
N1-C1 | 1.341(18) | 1.335 |
N1-C2 | 1.327(18) | 1.335 |
N2-N3 | 1.328(17) | 1.315 |
N2-C1 | 1.338(19) | 1.354 |
N3-C3 | 1.336(17) | 1.347 |
N4-N5 | 1.364(18) | 1.354 |
N4-C1 | 1.356(19) | 1.368 |
N5-C16 | 1.286(19) | 1.294 |
Bond Angles (°) | ||
C2-N1-C1 | 116.2(12) | 116.3 |
N3-N2-C1 | 118.1(12) | 116.9 |
N2-N3-C3 | 120.2(12) | 121.2 |
C1-N4-N5 | 119.4(12) | 123.1 |
C16-N5-N4 | 117.9(13) | 116.6 |
N1-C1-N4 | 119.3(13) | 120.6 |
N2-C1-N1 | 125.4(13) | 125.7 |
N2-C1-N4 | 115.2(13) | 113.5 |
N1-C2-C3 | 120.0(12) | 119.4 |
N1-C2-C4 | 114.6(12) | 115.1 |
N3-C3-C2 | 119.4(13) | 118.9 |
N3-C3-C10 | 115.0(12) | 114.7 |
O1-C18-C19 | 116.1(16) | 118.9 |
Bond Lengths (A°) Experimental B3LYP/6-31G (d, p) | ||
O1-C20 | 1.377(3) | 1.362 |
O1-C23 | 1.426(3) | 1.419 |
N1-C1 | 1.332(3) | 1.334 |
N1-C2 | 1.330(3) | 1.335 |
N2-N3 | 1.343(3) | 1.316 |
N2-C1 | 1.353(3) | 1.353 |
N3-C3 | 1.334(3) | 1.346 |
N4-N5 | 1.387(3) | 1.351 |
N4-C1 | 1.372(3) | 1.370 |
Bond Angles (°) | ||
C2-N1-C1 | 115.6(2) | 116.3 |
N3-N2-C1 | 117.3(2) | 116.7 |
N2-N3-C3 | 120.2(2) | 121.2 |
C1-N4-N5 | 121.9(2) | 121.9 |
C16-N5-N4 | 112.5(2) | 119.1 |
N1-C1-N4 | 122.1(2) | 119.7 |
N2-C1-N1 | 126.3(2) | 126.1 |
N2-C1-N4 | 111.6(3) | 114.0 |
N1-C2-C3 | 120.9(3) | 119.1 |
N1-C2-C4 | 115.5(2) | 115.3 |
N3-C3-C2 | 119.4(2) | 119.1 |
N3-C3-C10 | 113.9(2) | 114.7 |
C20-O1-C23 | 117.6(3) | 118.5 |
Bond Lengths (A°) Experimental B3LYP/6-31G (d, p) | ||
O1-C1 | 1.347(2) | 1.521 |
N1-C2 | 1.325(2) | 1.402 |
N2-N3 | 1.333(2) | 1.540 |
N2-C1 | 1.351(2) | 1.395 |
N3-C3 | 1.336(2) | 1.402 |
N4-N5 | 1.381(2) | 1.540 |
N4-C1 | 1.349(2) | 1.540 |
N5-C16 | 1.282(2) | 1.540 |
N6-C20 | 1.372(2) | 1.383 |
Bond Angles (°) | ||
C2-N1-C1 | 115.3(14) | 116.3 |
N3-N2-C1 | 118.3(13) | 119.9 |
N2-N3-C3 | 119.6(14) | 119.6 |
C1-N4-N5 | 122.4(14) | 109.4 |
C16-N5-N4 | 113.8(14) | 109.4 |
N1-C1-N4 | 120.7(15) | 120.9 |
N2-C1-N1 | 125.4(15) | 118.1 |
N2-C1-N4 | 113.7(14) | 120.9 |
N1-C2-C3 | 121.2(15) | 120.4 |
N1-C2-C4 | 116.5(15) | 119.1 |
N3-C3-C2 | 119.7(14) | 120.4 |
N3-C3-C10 | 116.5(14) | 119.1 |
Bond Lengths (A°) Experimental B3LYP/6-31G (d) | ||
O1-C18 | 1.357(4) | 1.341 |
N1-C1 | 1.336(3) | 1.334 |
N1-C2 | 1.337(3) | 1.336 |
N2-N3 | 1.338(3) | 1.317 |
N2-C1 | 1.338(3) | 1.350 |
N3-C3 | 1.339(3) | 1.346 |
N4-N5 | 1.383(3) | 1.351 |
N4-C1 | 1.360(3) | 1.371 |
N5-C16 | 1.271(3) | 1.291 |
Bond Angles (°) | ||
C2-N1-C1 | 115.9(2) | 116.3 |
N3-N2-C1 | 117.9(2) | 116.7 |
N2-N3-C3 | 120.4(2) | 121.2 |
C1-N4-N5 | 122.5(3) | 121.8 |
C16-N5-N4 | 115.1(2) | 119.2 |
N1-C1-N4 | 120.9(3) | 119.6 |
N2-C1-N1 | 126.0(3) | 126.1 |
N2-C1-N4 | 113.1(3) | 114.0 |
N1-C2-C3 | 120.4(2) | 119.0 |
N1-C2-C4 | 116.0(2) | 115.3 |
N3-C3-C2 | 119.1(2) | 119.1 |
N3-C3-C10 | 114.3(2) | 114.6 |
O1-C18-C19 | 118.3(3) | 115.8 |
2.4. Vibrational Analysis
1 | 2 | 3 | 4 | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Exp. B3LYP Assignment | Exp. B3LYP Assignment | Exp. B3LYP Assignment | Exp. B3LYP Assignment | ||||||||
1611 1517 | 1595 | ѴC=Carom | 1611 1513 | 1605 | ѴC=C | 1593 1507 | 1605 | ѴC=C | 1621 1515 | 1613 | ѴC=Carom |
1542 | ѴC=Narom | 1542 | ѴC=Narom | 1550 | ѴC=N | 1565 | ѴC=Carom | ||||
1512 | ѴC=Narom | 1511 | ѴC=Narom | 1538 | ѴC=Narom | 1536 | ѴC=Narom | ||||
1367 1280 | 1506 | ѴN=Carom | 1350 1247 | 1499 | ѴC=Carom | 1428 1363 | 1511 | ѴN=Carom | 1375 1279 | 1510 | ѴC=Narom |
1319 | ѴC-Carom | 1318 | ѴC-Carom | 1508 | ѴC=Narom | 1353 | βCHarom | ||||
1301 | ѴC-Carom | 1250 | ѴO-Ph | 1341 | ѴNPh | 1251 | ѴC-Carom | ||||
1239 | 1252 | ѴC-Carom | 1167 | 1127 | βCHarom | 1277 | 1257 | ѴC-Carom | 1133 | 1127 | ѴC=Narom |
1179 | 1127 | ѴC=Narom | 1126 | ѴC=Narom | 1171 | βCHarom | 1078 | 1081 | βCHarom | ||
1062 | 1061 | βCHarom | 1060 | 1080 | βCHarom | 1160 | 1126 | ѴC=Narom | 1062 | 1061 | βCHarom |
756 | 775 | βCHarom | 1060 | βCHarom | 1052 | 1079 | βCHarom | 750 | 724 | γCHarom | |
764 | 759 | γCHarom | 807 | 803 | γCHarom | 688 | 686 | γCHarom | |||
516 | 540 | γCHarom |
2.5. Nuclear Magnetic Resonance Studies (1H-NMR)
(1) | B3LYP (ppm) | (2) | B3LYP (ppm) | (3) | B3LYP (ppm) | (4) | B3LYP (ppm) |
---|---|---|---|---|---|---|---|
51H | 12.87 | 10H | 8.88 | 10H | 8.87 | 43H | 11.34 |
31H | 9.39 | 19H | 8.79 | 19H | 8.82 | 10H | 8.87 |
10H | 8.98 | 48H | 8.67 | 40H | 8.64 | 19H | 8.76 |
19H | 8.67 | 29H | 8.49 | 29H | 8.42 | 29H | 8.34 |
29H | 8.43 | 31H | 8.00 | 31H | 7.93 | 31H | 8.28 |
41H | 8.39 | 13H | 7.84 | 13H | 7.82 | 13H | 7.90 |
48H | 8.06 | 23H | 7.83 | 23H | 7.80 | 23H | 7.85 |
47H | 8.05 | 14H | 7.63 | 14H | 7.62 | 14H | 7.68 |
13H | 7.97 | 25H | 7.62 | 8H | 7.60 | 25H | 7.66 |
23H | 7.89 | 8H | 7.57 | 25H | 7.59 | 41H | 7.58 |
46H | 7.83 | 41H | 7.44 | 38H | 7.37 | 8H | 7.57 |
14H | 7.64 | 24H | 7.35 | 24H | 7.33 | 44H | 7.46 |
8H | 7.64 | 12H | 7.31 | 12H | 7.31 | 24H | 7.37 |
25H | 7.63 | 40H | 7.29 | 21H | 7.20 | 40H | 7.37 |
49H | 7.62 | 21H | 7.21 | 43H | 6.87 | 12H | 7.33 |
44H | 7.55 | 42H | 6.83 | 42H | 6.74 | 21H | 7.25 |
24H | 7.40 | 46H | 4.11 | 49H | 3.41 | 45H | 6.99 |
21H | 7.36 | 47H | 3.71 | 46H | 3.40 | ||
12H | 7.28 | 45H | 3.71 | 47H | 3.08 | ||
51H | 3.06 | ||||||
45H | 2.75 | ||||||
50H | 2.71 |
2.6. Frontier Molecular Orbital Analysis (FMO) and UV-Vis. Absorption Studies
Compound | E (HOMO) | E (LUMO) | ΔE (LUMO‒HOMO) |
---|---|---|---|
1 | −0.196 | −0.0713 | 0.124 |
2 | −0.196 | −0.064 | 0.132 |
3 | −0.18 | −0.060 | 0.119 |
4 | −0.204 | −0.072 | 0.133 |
Experimental | Theoretical (TD-SCF/B3LYP/6-31G (d, p)) | |||
---|---|---|---|---|
Compound | λmax (abs.) (DMSO) | λmax (osc. Strength), Gas Phase | λmax (osc. Strength) DMSO | Assignment |
(1) | 333 (0.419), 374 (0.454) | 380.8 (0.782) | 390.3 (0.945) | π‒π* |
(2) | 337 (1.903) | 345.2 (1.189) | 358.2 (1.401) | π‒π* |
(3) | 366 (2.834) | 370.4 (1.147) | 395.5 (1.196) | π‒π* |
(4) | 312 (0.567), 342 (0.697) | 350.2 (0.739) | 356.1 (1.007) | π‒π* |
2.7. Molecular Electrostatic Potential (MEP)
2.8. Hyperpolarizability and Non-Linear Optical Properties
Compound | 1 | 2 | 3 | 4 |
---|---|---|---|---|
βxxx | 2300.433 | 3639.217 | 8152.091 | 1281.031 |
βxxy | 6.139 | 41.559 | −559.94 | 223.445 |
βxyy | −520.79 | 207.2331 | −62.360 | −303.73 |
βyyy | −244.06 | −402.645 | −357.94 | −459.49 |
βxxz | 584.743 | 17.3065 | −46.037 | 40.0394 |
βxyz | 33.763 | 64.606 | 94.261 | 42.973 |
βyyz | 1.283 | −3.485 | −15.970 | 0.236 |
βxzz | 39.428 | 1.523 | −8.302 | 34.723 |
βyzz | 14.681 | 4.147 | 37.649 | 17.0493 |
βzzz | 9.201 | 9.715 | −8.129 | 7.664 |
βtot. (esu) | 16.647 | 29.797 | 70.233 | 8.957 |
2.9. Chemical Reactivity
Properties | 1 | 2 | 3 | 4 |
---|---|---|---|---|
ETotal (eV) | 0.124 | 0.132 | 0.119 | 0.133 |
EHOMO | −0.196 | −0.196 | −0.18 | −0.204 |
ELUMO | −0.0713 | −0.064 | −0.060 | −0.072 |
η (eV) | 0.062 | 0.066 | 0.059 | 0.066 |
µ (eV) | −0.133 | −0.13 | −0.120 | −0.138 |
ω (eV) | 0.142 | 0.128 | 0.119 | 0.143 |
µ(Debye) | 1.01 | 3.12 | 5.37 | 0.57 |
3. Experimental
3.1. General Information
3.2. Synthesis of 5,6-Diphenyl-4H-[1,2,4]triazine-3-thione
3.3. Synthesis of 3-Hydrazinyl-5,6-diphenyl-1,2,4-triazine
3.4. Synthesis of Compounds 1–4
3.5. Crystallography
3.6. Computational Details
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Arshad, M.N.; Bibi, A.; Mahmood, T.; Asiri, A.M.; Ayub, K. Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study. Molecules 2015, 20, 5851-5874. https://doi.org/10.3390/molecules20045851
Arshad MN, Bibi A, Mahmood T, Asiri AM, Ayub K. Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study. Molecules. 2015; 20(4):5851-5874. https://doi.org/10.3390/molecules20045851
Chicago/Turabian StyleArshad, Muhammad Nadeem, Aisha Bibi, Tariq Mahmood, Abdullah M. Asiri, and Khurshid Ayub. 2015. "Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study" Molecules 20, no. 4: 5851-5874. https://doi.org/10.3390/molecules20045851