Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts
Cyclopropylamine borane C<sub>3</sub>H<sub>5</sub>NH<sub>2</sub>BH<sub>3</sub> (C3AB), 2-ethyl-1-hexylamine borane CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(C<sub>2</sub>H<sub>5</sub>)CH<...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/3/1469 |
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| author | Kevin Turani-I-Belloto Rodica Chiriac François Toche Eddy Petit Pascal G. Yot Johan G. Alauzun Umit B. Demirci |
| author_facet | Kevin Turani-I-Belloto Rodica Chiriac François Toche Eddy Petit Pascal G. Yot Johan G. Alauzun Umit B. Demirci |
| author_sort | Kevin Turani-I-Belloto |
| collection | DOAJ |
| description | Cyclopropylamine borane C<sub>3</sub>H<sub>5</sub>NH<sub>2</sub>BH<sub>3</sub> (C3AB), 2-ethyl-1-hexylamine borane CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(C<sub>2</sub>H<sub>5</sub>)CH<sub>2</sub>NH<sub>2</sub>BH<sub>3</sub> (C2C6AB) and didodecylamine borane (C<sub>12</sub>H<sub>25</sub>)<sub>2</sub>NHBH<sub>3</sub> ((C12)2AB) are three new amine borane adducts (ABAs). They are synthesized by reaction of the corresponding amines with a borane complex, the reaction being exothermic as shown by Calvet calorimetry. The successful synthesis of each has been demonstrated by FTIR, Raman and NMR. For instance, the <sup>11</sup>B NMR spectra show the presence of signals typical of the NBH<sub>3</sub> environment, thereby implying the formation of B–N bonds. The occurrence of dihydrogen bonds (DHBs) for each of the ABAs has been highlighted by DSC and FTIR, and supported by DFT calculations (via the Mulliken charges for example). When heated, the three ABAs behave differently: C3AB and C2C6AB decompose from 68 to 100 °C whereas (C12)2AB is relatively stable up to 173 °C. That means that these ABAs are not appropriate as hydrogen carriers, but the ‘most’ stable (C12)2AB could open perspectives for the synthesis of advanced materials. |
| first_indexed | 2024-03-11T09:32:13Z |
| format | Article |
| id | doaj.art-417994dda5bf468abc4afac8bd3d2f98 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:32:13Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-417994dda5bf468abc4afac8bd3d2f982023-11-16T17:32:58ZengMDPI AGMolecules1420-30492023-02-01283146910.3390/molecules28031469Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane AdductsKevin Turani-I-Belloto0Rodica Chiriac1François Toche2Eddy Petit3Pascal G. Yot4Johan G. Alauzun5Umit B. Demirci6Institut Europeen des Membranes, IEM–UMR 5635, ENSCM, CNRS, Universite de Montpellier, 34090 Montpellier, FranceLaboratoire des Multimateriaux et Interfaces, UMR CNRS 5615, Université Claude Bernard Lyon 1, 69622 Villeurbanne, FranceLaboratoire des Multimateriaux et Interfaces, UMR CNRS 5615, Université Claude Bernard Lyon 1, 69622 Villeurbanne, FranceInstitut Europeen des Membranes, IEM–UMR 5635, ENSCM, CNRS, Universite de Montpellier, 34090 Montpellier, FranceICGM, Universite de Montpellier, CNRS, ENSCM, 34293 Montpellier, FranceICGM, Universite de Montpellier, CNRS, ENSCM, 34293 Montpellier, FranceInstitut Europeen des Membranes, IEM–UMR 5635, ENSCM, CNRS, Universite de Montpellier, 34090 Montpellier, FranceCyclopropylamine borane C<sub>3</sub>H<sub>5</sub>NH<sub>2</sub>BH<sub>3</sub> (C3AB), 2-ethyl-1-hexylamine borane CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(C<sub>2</sub>H<sub>5</sub>)CH<sub>2</sub>NH<sub>2</sub>BH<sub>3</sub> (C2C6AB) and didodecylamine borane (C<sub>12</sub>H<sub>25</sub>)<sub>2</sub>NHBH<sub>3</sub> ((C12)2AB) are three new amine borane adducts (ABAs). They are synthesized by reaction of the corresponding amines with a borane complex, the reaction being exothermic as shown by Calvet calorimetry. The successful synthesis of each has been demonstrated by FTIR, Raman and NMR. For instance, the <sup>11</sup>B NMR spectra show the presence of signals typical of the NBH<sub>3</sub> environment, thereby implying the formation of B–N bonds. The occurrence of dihydrogen bonds (DHBs) for each of the ABAs has been highlighted by DSC and FTIR, and supported by DFT calculations (via the Mulliken charges for example). When heated, the three ABAs behave differently: C3AB and C2C6AB decompose from 68 to 100 °C whereas (C12)2AB is relatively stable up to 173 °C. That means that these ABAs are not appropriate as hydrogen carriers, but the ‘most’ stable (C12)2AB could open perspectives for the synthesis of advanced materials.https://www.mdpi.com/1420-3049/28/3/1469adductamine boraneboranesboron chemistrydihydrogen bonds |
| spellingShingle | Kevin Turani-I-Belloto Rodica Chiriac François Toche Eddy Petit Pascal G. Yot Johan G. Alauzun Umit B. Demirci Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts Molecules adduct amine borane boranes boron chemistry dihydrogen bonds |
| title | Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts |
| title_full | Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts |
| title_fullStr | Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts |
| title_full_unstemmed | Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts |
| title_short | Synthesis: Molecular Structure, Thermal-Calorimetric and Computational Analyses, of Three New Amine Borane Adducts |
| title_sort | synthesis molecular structure thermal calorimetric and computational analyses of three new amine borane adducts |
| topic | adduct amine borane boranes boron chemistry dihydrogen bonds |
| url | https://www.mdpi.com/1420-3049/28/3/1469 |
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