As a supplier of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE, I am often asked about the spectroscopic characteristics of this compound. In this blog post, I will delve into the various spectroscopic aspects of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE, providing a comprehensive overview for those interested in its analysis and application.
1. Introduction to N,N'-DI-TERT-BUTYLETHYLENEDIAMINE
N,N'-DI-TERT-BUTYLETHYLENEDIAMINE is an organic compound with the molecular formula C₁₀H₂₄N₂. It is a colorless to pale - yellow liquid with a characteristic amine odor. This compound is widely used in various chemical processes, including as a ligand in coordination chemistry and as a building block in organic synthesis.
2. Nuclear Magnetic Resonance (NMR) Spectroscopy
2.1 Proton NMR (¹H - NMR)
The ¹H - NMR spectrum of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE provides valuable information about the hydrogen atoms in the molecule.
- tert - Butyl groups: The six equivalent methyl groups of the two tert - butyl moieties appear as a singlet in the ¹H - NMR spectrum. Typically, this singlet is observed around 1.0 - 1.2 ppm. The high - field shift is due to the shielding effect of the electron - rich carbon atoms in the tert - butyl groups.
- Ethylene bridge protons: The four protons on the ethylene bridge (-CH₂ - CH₂ -) between the two nitrogen atoms usually give a multiplet or a set of signals in the range of 2.5 - 3.0 ppm. The chemical shift is influenced by the electron - withdrawing effect of the adjacent nitrogen atoms.
The integration of the peaks in the ¹H - NMR spectrum can be used to confirm the ratio of the different types of hydrogen atoms in the molecule. For N,N'-DI-TERT-BUTYLETHYLENEDIAMINE, the ratio of the protons from the tert - butyl groups to the ethylene bridge protons is 18:4, which is consistent with the molecular structure.
2.2 Carbon - 13 NMR (¹³C - NMR)
The ¹³C - NMR spectrum of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE reveals information about the carbon atoms in the molecule.
- tert - Butyl carbons: The three equivalent methyl carbons of each tert - butyl group appear as a single peak around 28 - 30 ppm. The quaternary carbon in the tert - butyl group, which is directly attached to the nitrogen atom, has a distinct chemical shift around 50 - 52 ppm.
- Ethylene bridge carbons: The two carbon atoms in the ethylene bridge are observed around 45 - 48 ppm. The chemical shift is affected by the neighboring nitrogen atoms and the overall electronic environment of the molecule.
3. Infrared (IR) Spectroscopy
The IR spectrum of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE contains several characteristic absorption bands that can be used to identify the functional groups in the molecule.
- N - H stretching vibrations: The N - H bonds in the amine groups exhibit stretching vibrations in the range of 3200 - 3500 cm⁻¹. In N,N'-DI-TERT-BUTYLETHYLENEDIAMINE, these bands are often broad and medium - to - strong in intensity. The presence of hydrogen bonding between the amine groups can further broaden and shift these bands.
- C - H stretching vibrations: The C - H bonds in the tert - butyl and ethylene groups show stretching vibrations. The C - H stretching of the methyl groups in the tert - butyl moieties occurs around 2960 - 2870 cm⁻¹, while the C - H stretching of the ethylene bridge appears in a similar range but with slightly different intensities and shapes.
- C - N stretching vibrations: The C - N bonds in the molecule have stretching vibrations in the range of 1000 - 1300 cm⁻¹. These bands are relatively weak but can still be used as part of the overall fingerprint region for the compound.
4. Mass Spectrometry (MS)
The mass spectrum of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE provides information about the molecular weight and the fragmentation pattern of the molecule.
- Molecular ion peak: The molecular ion peak (M⁺) in the mass spectrum of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE corresponds to the molecular weight of the compound, which is 172 g/mol. However, due to the relatively high stability of the molecule, the molecular ion peak may not be very intense.
- Fragmentation patterns: Common fragmentation pathways include the loss of a tert - butyl group, resulting in a fragment with a mass of 114 g/mol. Further fragmentation can occur, leading to the formation of smaller fragments such as those containing the ethylene bridge and amine groups.
5. Ultraviolet - Visible (UV - Vis) Spectroscopy
N,N'-DI-TERT-BUTYLETHYLENEDIAMINE does not have significant chromophores that absorb strongly in the UV - Vis region. As a result, its UV - Vis spectrum typically shows only weak absorption in the far - UV region (below 200 nm), which is mainly due to the n - σ* transitions of the lone pairs on the nitrogen atoms and the C - H and C - N bonds.
6. Applications in the Chemical Industry
The knowledge of the spectroscopic characteristics of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE is crucial in its various applications.
- Organic synthesis: In organic synthesis, NMR and IR spectroscopy can be used to monitor the progress of reactions involving N,N'-DI-TERT-BUTYLETHYLENEDIAMINE. For example, if it is used as a ligand in a metal - catalyzed reaction, the spectroscopic changes can indicate the formation of the metal - ligand complex.
- Quality control: Spectroscopic techniques are essential for quality control in the production of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE. By comparing the experimental spectra with the reference spectra, impurities can be detected, and the purity of the product can be determined.
7. Related Compounds and Their Spectroscopic Comparisons
It is interesting to compare the spectroscopic characteristics of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE with related compounds. For example, Di - N - hexylamine and 4,6 - dihydroxypyrimidine have different molecular structures and thus different spectroscopic features.
- Di - N - hexylamine: This compound has a different alkyl chain length compared to N,N'-DI-TERT-BUTYLETHYLENEDIAMINE. In the ¹H - NMR spectrum, the protons on the hexyl chains will show a more complex pattern due to the longer carbon chain. The IR spectrum may also have different C - H stretching vibrations depending on the conformation and the number of methylene groups in the hexyl chains.
- 4,6 - dihydroxypyrimidine: This is a heterocyclic compound with hydroxyl groups. Its NMR and IR spectra will be dominated by the signals from the pyrimidine ring and the hydroxyl groups. The ¹H - NMR spectrum will show characteristic signals for the ring protons, and the IR spectrum will have strong O - H stretching vibrations in the 3200 - 3600 cm⁻¹ region.
Another related compound is 1 - naphthaleneboronic Acid. It has a naphthalene ring system and a boronic acid group. The UV - Vis spectrum of 1 - naphthaleneboronic acid will show strong absorption in the UV region due to the π - π* transitions in the naphthalene ring, which is quite different from the weak UV absorption of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE.
8. Conclusion and Call to Action
In conclusion, the spectroscopic characteristics of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE are diverse and provide a wealth of information about its molecular structure and properties. NMR, IR, MS, and UV - Vis spectroscopy are all powerful tools for analyzing this compound.
As a reliable supplier of N,N'-DI-TERT-BUTYLETHYLENEDIAMINE, we ensure the high quality of our product. Our in - house quality control team uses advanced spectroscopic techniques to guarantee the purity and consistency of every batch. If you are interested in purchasing N,N'-DI-TERT-BUTYLETHYLENEDIAMINE for your research or industrial applications, please contact us for more information and to discuss your specific requirements. We look forward to working with you to meet your chemical needs.
References
- Silverstein, R. M., Webster, F. X., & Kiemle, D. J. (2014). Spectrometric Identification of Organic Compounds. John Wiley & Sons.
- Pavia, D. L., Lampman, G. M., Kriz, G. S., & Vyvyan, J. R. (2015). Introduction to Spectroscopy: A Guide for Students of Organic Chemistry. Cengage Learning.