Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety
A new asymmetrical tripodal amine, [H3L2]Br3 containing morpholine moiety was prepared from reacting of one equivalent of N-(3-aminopropyl)morpholine and two equivalents of tosylaziridine, followed by detosylation with HBr/CH3COOH. The products were characterized by various spectroscopic methods suc...
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| Format: | Article |
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Elsevier
2016-11-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535212000925 |
| _version_ | 1818267105695367168 |
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| author | Majid Rezaeivala Sadegh Salehzadeh Hassan Keypour Seik Weng Ng Laura Valencia |
| author_facet | Majid Rezaeivala Sadegh Salehzadeh Hassan Keypour Seik Weng Ng Laura Valencia |
| author_sort | Majid Rezaeivala |
| collection | DOAJ |
| description | A new asymmetrical tripodal amine, [H3L2]Br3 containing morpholine moiety was prepared from reacting of one equivalent of N-(3-aminopropyl)morpholine and two equivalents of tosylaziridine, followed by detosylation with HBr/CH3COOH. The products were characterized by various spectroscopic methods such as FAB-MS, elemental analysis, 1H and 13C NMR spectroscopy. The crystal structure of the hydrobromide salt of the latter amine, [H3L2]Br3, was also determined. For triprotonated form of the ligand L2 we can consider several microspecies and/or conformers. A theoretical study at B3LYP/6-31G∗∗ level of theory showed that the characterized microspecies is the most stable microspecies for the triprotonated form of the ligand. It was shown that the experimental NMR data for [H3L2]Br3 in solution have good correlation with the corresponding calculated data for the most stable microspecies of [H3L2]3+ in the gas phase. |
| first_indexed | 2024-12-12T20:17:19Z |
| format | Article |
| id | doaj.art-b4f20ee86439458ca55776af2f5c97a5 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-12T20:17:19Z |
| publishDate | 2016-11-01 |
| publisher | Elsevier |
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| series | Arabian Journal of Chemistry |
| spelling | doaj.art-b4f20ee86439458ca55776af2f5c97a52022-12-22T00:13:21ZengElsevierArabian Journal of Chemistry1878-53522016-11-019S2S1610S161710.1016/j.arabjc.2012.04.024Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moietyMajid Rezaeivala0Sadegh Salehzadeh1Hassan Keypour2Seik Weng Ng3Laura Valencia4Department of Chemical Engineering, Hamedan University of Technology, Hamedan 65155, IranFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, IranFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, IranDepartment of Chemistry,University of Malaya, 50603 Kuala Lumpur, MalaysiaDepartamento de Quımica Inorganica, Facultad de Quımica, Universidad de Vigo, 36310 Vigo, Pontevedra, SpainA new asymmetrical tripodal amine, [H3L2]Br3 containing morpholine moiety was prepared from reacting of one equivalent of N-(3-aminopropyl)morpholine and two equivalents of tosylaziridine, followed by detosylation with HBr/CH3COOH. The products were characterized by various spectroscopic methods such as FAB-MS, elemental analysis, 1H and 13C NMR spectroscopy. The crystal structure of the hydrobromide salt of the latter amine, [H3L2]Br3, was also determined. For triprotonated form of the ligand L2 we can consider several microspecies and/or conformers. A theoretical study at B3LYP/6-31G∗∗ level of theory showed that the characterized microspecies is the most stable microspecies for the triprotonated form of the ligand. It was shown that the experimental NMR data for [H3L2]Br3 in solution have good correlation with the corresponding calculated data for the most stable microspecies of [H3L2]3+ in the gas phase.http://www.sciencedirect.com/science/article/pii/S1878535212000925Morpholine moietyTripodal amine1H and 13C NMR spectroscopyX-ray crystal structureTheoretical study |
| spellingShingle | Majid Rezaeivala Sadegh Salehzadeh Hassan Keypour Seik Weng Ng Laura Valencia Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety Arabian Journal of Chemistry Morpholine moiety Tripodal amine 1H and 13C NMR spectroscopy X-ray crystal structure Theoretical study |
| title | Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| title_full | Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| title_fullStr | Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| title_full_unstemmed | Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| title_short | Synthesis, characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| title_sort | synthesis characterization and theoretical study of a new asymmetrical tripodal amine containing morpholine moiety |
| topic | Morpholine moiety Tripodal amine 1H and 13C NMR spectroscopy X-ray crystal structure Theoretical study |
| url | http://www.sciencedirect.com/science/article/pii/S1878535212000925 |
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