Syntheses, Structures and Antimicrobial Activities of bis(Imino)acenaphthene (BIAN) Imidazolium Salts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Syntheses of L, 2, 3, 4 and 5
2.2. X-ray Crystal Structures of L, 2, 4 and 5
L | 2 | 4 | 5 | |
---|---|---|---|---|
Formula | C36H40N2 | C33H35Cl3N2O | C26H17Cl3F2N2 | C37H42Cl2N2 |
Formula weight | 500.70 | 581.98 | 501.77 | 585.63 |
Crystal system | Monoclinic | Monoclinic | Monoclinic | Monoclinic |
Space group | C2/c | P21/c | P21/c | P21/c |
a/Å | 31.987(3) | 12.7377(12) | 10.104(3) | 17.047(4) |
b/Å | 9.0070(9) | 14.4165(13) | 24.514(7) | 12.711(3) |
c/Å | 10.3906(10) | 16.2893(14) | 9.243(2) | 14.823(4) |
α/° | 90.0 | 90.0 | 90.0 | 90.0 |
β/° | 105.809(4) | 91.280(3) | 94.103(3) | 90.142(5) |
γ/° | 90.0 | 90.0 | 90.0 | 90.0 |
Z | 4 | 4 | 4 | 4 |
Dc/g cm-3 | 1.155 | 1.293 | 1.459 | 1.211 |
F(000) | 1080 | 1224 | 1024 | 1248 |
Crystal size/nm | 0.24 × 0.18 × 0.06 | 0.16 × 0.14 × 0.11 | 0.26 × 0.16 × 0.14 | 0.23 × 0.20 × 0.09 |
Θ range/° | 3.00–27.48 | 3.00–25.00 | 2.02–27.50 | 2.99–25.00 |
Collected reflections | 29622 | 24514 | 25427 | 19946 |
Independent reflns | 3304 | 5172 | 5213 | 5644 |
Rint | 0.0602 | 0.1143 | 0.0583 | 0.0808 |
R1 [I>2σ(I)] | 0.0502 | 0.0529 | 0.0567 | 0.0878 |
wR2 (all data) | 0.1226 | 0.1375 | 0.1785 | 0.2421 |
Bond distances/Å | 2 | 4 | 5 |
C(1)-N(1) | 1.351(3) | 1.347(3) | 1.339(5) |
C(1)-N(2) | 1.346(3) | 1.345(3) | 1.341(5) |
C(2)-C(3) | 1.368(4) | 1.371(3) | 1.350(6) |
C(2)-N(1) | 1.375(3) | 1.383(3) | 1.386(5) |
C(3)-N(2) | 1.390(3) | 1.383(3) | 1.385(5) |
Bond angles/° | 2 | 4 | 5 |
N(1)-C(1)-N(2) | 109.5(2) | 109.08(18) | 110.0(4) |
N(1)-C(2)-C(3) | 107.8(2) | 107.45(19) | 107.2(4) |
C(2)-C(3)-N(2) | 107.3(2) | 107.10(19) | 108.3(4) |
C(1)-N(1)-C(2) | 107.8(2) | 108.03(18) | 107.5(4) |
C(1)-N(2)-C(3) | 107.6(2) | 108.33(17) | 106.9(4) |
2.3. Antimicrobial Testing of Compounds 1-5
Microbial spp. | ||||
---|---|---|---|---|
Compound | S. aureus | B. subtilis | E. coli | P. aeruginosa |
1 | <0.6 | <0.6 | 39.06 | 39.06 |
2 | <0.6 | <0.6 | 78.12 | 39.06 |
3 | 1.22 | 4.88 | 312.55 | >312.55 |
4 | 19.53 | 39.06 | >312.55 | >312.55 |
5 | 9.76 | 9.76 | >312.55 | >312.55 |
3. Experimental
3.1. General
3.2. Physical measurements
3.3. Preparations
3.4. X-ray crystallography
3.5. Antimicrobial studies
4. Conclusions
Acknowledgements
References and Notes
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Butorac, R.R.; Al-Deyab, S.S.; Cowley, A.H. Syntheses, Structures and Antimicrobial Activities of bis(Imino)acenaphthene (BIAN) Imidazolium Salts. Molecules 2011, 16, 3168-3178. https://doi.org/10.3390/molecules16043168
Butorac RR, Al-Deyab SS, Cowley AH. Syntheses, Structures and Antimicrobial Activities of bis(Imino)acenaphthene (BIAN) Imidazolium Salts. Molecules. 2011; 16(4):3168-3178. https://doi.org/10.3390/molecules16043168
Chicago/Turabian StyleButorac, Rachel R., Salem S. Al-Deyab, and Alan H. Cowley. 2011. "Syntheses, Structures and Antimicrobial Activities of bis(Imino)acenaphthene (BIAN) Imidazolium Salts" Molecules 16, no. 4: 3168-3178. https://doi.org/10.3390/molecules16043168