Trivinylphosphine Oxide: Synthesis, Characterization, and Polymerization Reactivity Investigated Using Single-Crystal Analysis and Density Functional Theory
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Structural Analysis
2.2. DFT Calculations
2.2.1. Nucleophilic Addition Reaction (Pseudo-Michael Addition) Using Piperazine
2.2.2. Anionic Addition Reaction Using a Grignard Reagent
3. Materials and Methods
3.1. Materials
3.2. NMR Spectroscopy
3.3. Single-Crystal X-ray Analysis
3.4. Computational Methods
3.5. Synthesis of Trivinylphosphine Oxide (TVPO)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Identification Code | TVPO (CCDC 2260460) | TVPO (CCDC 1277428) [15] |
---|---|---|
Empirical formula | C6H9OP | C6H9OP |
Formula weight | 128.10 | 128.10 |
Temperature (K) | 173.15 | 143 |
Crystal system | Orthorhombic | Orthorhombic |
Space group | Pnma | Pnma |
a (Å) | 9.4940 (7) | 9.5130 (2) |
b (Å) | 10.7754 (12) | 10.7830 (3) |
c (Å) | 7.0590 (6) | 7.0590 (3) |
α (°) | 90 | 90 |
β (°) | 90 | 90 |
γ (°) | 90 | 90 |
Volume (Å3) | 722.15 (11) | 724.10 (4) |
Z | 4 | 4 |
ρcalc (g/cm3) | 1.178 | 1.175 |
μ (mm−1) | 0.286 | 0.286 |
F(000) | 272.0 | 272.0 |
Crystal size (mm3) | 0.5 × 0.3 × 0.2 | 0.5 × 0.20 × 0.15 |
Radiation | MoKα (λ = 0.71073) | MoKα (λ = 0.71073) |
2Θ Range for data collection (°) | 6.9 to 51.168 | 3.45 to 27.60 |
Index ranges | −10 ≤ h ≤ 11 −12 ≤ k ≤ 13 −8 ≤ l ≤ 8 | 0 ≤ h ≤ 12 0 ≤ k ≤ 14 0 ≤ l ≤ 8 |
Reflections collected | 2929 | 25094 |
Independent reflections | 723 [Rint = 0.0424, Rsigma = 0.0240] | 839 [Rint = 0.036] |
Data/restraints/parameters | 723/0/437 | 839/0/65 |
Goodness-of-fit on F2 | 1.213 | 1.092 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0275, wR2 = 0.0673 | R1 = 0.0353, wR2 = 0.1030 |
Final R indexes [all data] | R1 = 0.0327, wR2 = 0.0855 | R1 = 0.0355, wR2 = 0.1032 |
Largest diff. peak/hole (e Å−3) | 0.22/−0.44 | 0.258/−0.305 |
CCDC 2260460 a | CCDC 1277428 b | Calculated, This Study c | |
---|---|---|---|
P−O | 1.486 (2) | 1.5004 (13) | 1.503 |
P−C1 | 1.7886 (18) | 1.796 (2) | 1.792 |
P−C3 | 1.787 (3) | 1.7929 (14) | 1.791 |
C1−C5 | 1.310 (3) | 1.316 (3) | 1.314 |
C2−C3 | 1.313 (4) | 1.321 (2) | 1.320 |
O···H2A | 2.7165 (15) | 2.78 (4) | 2.743 |
O···H5A | 2.7065 (8) | 2.75 (3) | 2.731 |
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Salmeia, K.A.; Afaneh, A.T.; Habash, R.R.; Neels, A. Trivinylphosphine Oxide: Synthesis, Characterization, and Polymerization Reactivity Investigated Using Single-Crystal Analysis and Density Functional Theory. Molecules 2023, 28, 6097. https://doi.org/10.3390/molecules28166097
Salmeia KA, Afaneh AT, Habash RR, Neels A. Trivinylphosphine Oxide: Synthesis, Characterization, and Polymerization Reactivity Investigated Using Single-Crystal Analysis and Density Functional Theory. Molecules. 2023; 28(16):6097. https://doi.org/10.3390/molecules28166097
Chicago/Turabian StyleSalmeia, Khalifah A., Akef T. Afaneh, Reem R. Habash, and Antonia Neels. 2023. "Trivinylphosphine Oxide: Synthesis, Characterization, and Polymerization Reactivity Investigated Using Single-Crystal Analysis and Density Functional Theory" Molecules 28, no. 16: 6097. https://doi.org/10.3390/molecules28166097