Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate
Abstract
:Introduction
Results and Discussion
Determination of the most stable tautomeric form of compound 1 by a computational approach.
Tautomer | Ionization potential | Dipole moment, D | Heat of formation, ∆Hf , (kcal/mol) |
---|---|---|---|
A | 8.75 | 6.80 | 15.14 |
B | 8.91 | 2.79 | 7.09 |
C | 9.74 | 4.45 | 10.41 |
Conclusions
Experimental
General
X-ray structural analysis
Parameter | 1 | 2 |
---|---|---|
Empirical formula | C13H11N3O2 | C14H13N3O2 |
Formula weight | 241.25 | 255.27 |
Crystal size (mm) | 0.90 х 0.80 х 0.10 | 0.80 х 0.30 х 0.20 |
Crystal system | Monoclinic | Triclinic |
Space group | P 21/с | P-1 |
Z | 4 | 2 |
a, Å | 7.970(6) | 8.196(5) |
b, Å | 7.061(2) | 8.997(6) |
c, Å | 20.537(7) | 9.435(4) |
α | 90 | 74.22(4) |
β | 97.69(5) | 89.75(4) |
γ | 90 | 74.07(5) |
V, Å3 | 1145.3(10) | 641.9(6) |
dcall, g/cm3 | 1.399 | 1.321 |
Theta range | 2.4<θ<26.0° | 2.3<θ<26.0° |
μexp (cm-1) | 0.098 | 0.091 |
Reflections collected | 2247 | 2526 |
Number of reflections with | 1644 | 1674 |
I>2σ (I) | ||
R1 (I>2σ(I) and for all) | 0.0523 (0.0777) | 0.0714 (0.1092) |
WR2 (I>2σ(I) and for all) | 0.1197 (0.1387) | 0.1539 (0.1821) |
Max. diff. peak and hole | 0.166 and –0.181 eÅ-3 | 0.209 и –0.261 eÅ-3 |
Acknowledgments
References
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Tulyasheva, M.; Rasulev, B.; Tojiboev, A.; Turgunov, K.; Tashkhodjaev, B.; Abdullaev, N.; Shakhidoyatov, K. Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate. Molecules 2005, 10, 1209-1217. https://doi.org/10.3390/10091209
Tulyasheva M, Rasulev B, Tojiboev A, Turgunov K, Tashkhodjaev B, Abdullaev N, Shakhidoyatov K. Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate. Molecules. 2005; 10(9):1209-1217. https://doi.org/10.3390/10091209
Chicago/Turabian StyleTulyasheva, M., B. Rasulev, A. Tojiboev, K. Turgunov, B. Tashkhodjaev, N. Abdullaev, and K Shakhidoyatov. 2005. "Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate" Molecules 10, no. 9: 1209-1217. https://doi.org/10.3390/10091209