Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn
Abstract
1. Introduction
2. Results and Discussion
2.1. Molecular Design and Synthesis
2.2. Structural Analysis
2.3. Thermal Analysis of the Eleven-Membered Ring Systems
3. Materials and Methods
3.1. General Information
3.2. Computational Details
3.3. Syntheses
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: There are no samples available. |
9b (E = Ge) | 9c (E = Sn) | |
---|---|---|
Bond Lengths/pm | ||
E1–C1 | 194.0(1) | 213.1(2) |
E1–C7 | 194.4(1) | 213.4(2) |
E1–C22 | 194.7(1) | 213.2(2) |
E1–C23 | 194.6(1) | 214.6(2) |
Bond Angels/° | ||
C1–E1–C7 | 112.56(5) | 110.78(7) |
C1–E1–C22 | 108.82(5) | 104.33(7) |
C1–E1–C23 | 109.72(5) | 109.98(7) |
C7–E1–C23 | 107.94(5) | 103.67(7) |
C22–E1–C7 | 110.65(5) | 123.99(7) |
C22–E1–C23 | 107.01(5) | 103.47(7) |
C13–O2–C18 | 114.20(1) | 117.35(1) |
O1–C12–C13 | 116.20(1) | 122.18(1) |
O1–C12–C17 | 124.10(1) | 117.70(1) |
O2–C13–C12 | 120.60(1) | 115.74(1) |
O2–C13–C14 | 119.20(1) | 124.60(1) |
O2–C18–C19 | 107.80(1) | 113.16(1) |
Torsion Angels/° | ||
C7–E1–C1–C2 | −131.7(1) | −156.3(1) |
C7–E1–C1–C6 | 50.0(1) | 27.3(2) |
C22–E1–C1–C2 | −8.7(1) | −20.7(2) |
C22–E1–C1–C6 | 173.1(1) | 162.9(2) |
C1–E1–C7–S1 | −158.5(7) | −128.3(1) |
C22–E1–C7–S1 | 79.4(8) | 106.6(1) |
C1–E1–C22–S2 | 77.6(8) | 107.1(1) |
C7–E1–C22–S2 | −158.2(7) | −125.0(1) |
C23–E1–C22–S2 | −40.8(8) | −8.0(1) |
C23–E1–C22–C19 | 147.0(1) | −172.4(2) |
C11–O1–C12–C13 | −147.2(1) | −56.9(2) |
C11–O1–C12–C17 | 39.1(2) | 129.7(2) |
C18–O2–C13–C12 | 68.5(1) | −163.8(2) |
C18–O2–C13–C14 | −116.7(1) | 14.2(3) |
Atom | C | Si | Ge | Sn |
---|---|---|---|---|
ΔE (kJ/mol), native | −312.9 | −131.8 | −65.5 | 172.8 |
ΔE (kJ/mol), methylene | −359.8 | −190.5 | −127.1 | 103.2 |
TGA (Accuracy ± 0.5 °C) | DSC (Accuracy ± 0.2 °C) | ||||||
---|---|---|---|---|---|---|---|
Sample | Td1(onset)/°C | Td1f(endset)/°C | Loss/% | Tm(onset)/°C | Tm(endset)/°C | Normalized Enthalpy | |
/(J/g) | /(kJ/mol) | ||||||
Si-Ring (6a) | 290.2 | 302.2 | 14 | 105.4 | 113.4 | 5.96 | 2.87 |
Ge-Ring (6b) | 277.6 | 300.3 | 12 | 110.8 | 116 | 46.88 | 24.71 |
Sn-Ring (6c) | 231.8 | 240.4 | 13 | 118.5 | 120.7 | 1.73 | 0.99 |
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Eleya, N.; Appiah, C.; Lork, E.; Gogolin, M.; Gesing, T.M.; Stauch, T.; Staubitz, A. Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn. Molecules 2020, 25, 283. https://doi.org/10.3390/molecules25020283
Eleya N, Appiah C, Lork E, Gogolin M, Gesing TM, Stauch T, Staubitz A. Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn. Molecules. 2020; 25(2):283. https://doi.org/10.3390/molecules25020283
Chicago/Turabian StyleEleya, Nadi, Clement Appiah, Enno Lork, Mathias Gogolin, Thorsten M. Gesing, Tim Stauch, and Anne Staubitz. 2020. "Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn" Molecules 25, no. 2: 283. https://doi.org/10.3390/molecules25020283
APA StyleEleya, N., Appiah, C., Lork, E., Gogolin, M., Gesing, T. M., Stauch, T., & Staubitz, A. (2020). Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn. Molecules, 25(2), 283. https://doi.org/10.3390/molecules25020283