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Molecules 2016, 21, 24 4 of 11 the longer alkyl backbones of hexyl and decylamine, while integration of the peaks further evidenced its structure and purity. Table 1. Percentage yields of the n-phenyl–n-alkyl ureas of for pure, protected and de-protected amine. Amine n Percentage Yield (%) Non-Protected Protected De-Protected Molecules 2016, 21, 24 Hexylamine Propylamine 1 95 4 85 8 91 28 85 20 80 38 93 4 of 10 differences in spectra were the chemical shifts at 1.3 ppm attributed to the longer alkyl backbones of Decylamine Octadecylamine 16 90 69 72 hexyl and decylamine, while integration of the peaks further evidenced its structure and purity. The urea melting temperatures (Tm) were determined by DSC (Table 2). All measured values The urea melting temperatures (Tm) were determined by DSC (Table 2). All measured values correlated well with literature values and possessed small melting temperature ranges, indicating correlated well with literature values and possessed small melting temperature ranges, indicating high high purity [41]. The n-propyl urea exhibited the highest melting point and crystallization temperature purity [41]. The n-propyl urea exhibited the highest melting point and crystallization temperature despite the shortest carbon chain, and highest volatility. Similarly, the propyl and hexyl carbamates despite the shortest carbon chain, and highest volatility. Similarly, the propyl and hexyl carbamates showed an increase in the decomposition onset temperature due to the stronger charged carbamate showed an increase in the decomposition onset temperature due to the stronger charged carbamate interactions present. The ureas contain hydrogen bonding donors (NH2) and hydrogen bonding interactions present. The ureas contain hydrogen bonding donors (NH2) and hydrogen bonding acceptors (C=O). The shorter alkyl chains contribute less steric hindrance and thus, a higher degree acceptors (C=O). The shorter alkyl chains contribute less steric hindrance and thus, a higher degree of hydrogen bonding occurs. As the chain length increases, the alkyl chain disrupts the urea-urea of hydrogen bonding occurs. As the chain length increases, the alkyl chain disrupts the urea-urea hydrogen bonding and order, thus reducing the melting point, as seen with n-hexyl urea (68–69 °C). ̋As hydrogen bonding and order, thus reducing the melting point, as seen with n-hexyl urea (68–69 C). the alkyl chain increases, an expected Tm increase from 82 °C for ̋ decylamine to 95 °C for ̋stearyl amine As the alkyl chain increases, an expected Tm increase from 82 C for decylamine to 95 C for stearyl is observed, which is due to increases in energy demand for the onset of melting for higher molecular amine is observed, which is due to increases in energy demand for the onset of melting for higher weight urea. molecular weight urea. Table 2. n-Phenyl, n-alkyl urea melting points and crystallization temperatures determine from DSC. Table 2. n-Phenyl, n-alkyl urea melting points and crystallization temperatures determine from DSC. Entry MP (°C) Recrystalization Temp. (°C) Entry MP ( ̋C) 112–114 Recrystalization Temp. ( ̋C) n-phenyl, n-propyl urea n-phenyl, n-propyl urea n-phenyl, n-hexyl urea n-phenyl, n-hexyl urea n-phenyl, n-decyl urea n-phenyl, n-decyl urea n-phenyl, n-stearyl urea n-phenyl, n-stearyl urea 112–114 89 47 61 84 89 47 61 84 68–70 68–70 81–83 81–83 95–97 95–97 for each urea isolated. From the image, we can further conclude urea purity consistency throughout each amine state. As with the FTIR data, Figure 1 displays a typical DSC curve used to determine T Figure 1 displays a typical DSC curve used to determine Tm for each urea isolated. From the image, we can further conclude urea purity consistency throughout each amine state. As with the FTIR data, the protected and de-protected samples all provide isolated products which are chemically identical. the protected and de-protected samples all provide isolated products which are chemically identical. Figure 1. DSC spectra of n-propyl urea isolated from all three amine starting materials. Ramp rate = Figure 1. DSC spectra of n-propyl urea isolated from all three amine starting materials. Ramp 5 °C per ̋minute to 140 °C follo ̋wed by equilibration to 60 °C and ̋repeated heating. rate = 5 C per minute to 140 C followed by equilibration to 60 C and repeated heating. 2.2. Synthesis of n-Propyl, Benzophenone(BP) Imine Titanium(IV) isopropoxide is a low cost mediator in BP imine synthesis [42–46]. According to Figure 2, the initial BP concentration of 0.45 M is slowly reduced to 0.26 M after 3 h and finally 0.11 M after 24 h as the reaction proceeds. Gas chromatography (GC) was used to determine an overall yield of 75% for the non-protected amine while a 25% yield is obtained for the protected and 50% forPDF Image | Amines vs Nucleophilic Substitution Reversible Reaction CO2
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