Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer
Malondialdehyde (MDA) engages in a triel bond (TrB) with TrX<sub>3</sub> (Tr = B and Al; X = H, F, Cl, and Br) in three modes, in which the hydroxyl O, carbonyl O, and central carbon atoms of MDA act as the electron donors, respectively. A H···X secondary interaction coexists with the Tr...
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MDPI AG
2022-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/18/6091 |
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| author | Qiaozhuo Wu Shubin Yang Qingzhong Li |
| author_facet | Qiaozhuo Wu Shubin Yang Qingzhong Li |
| author_sort | Qiaozhuo Wu |
| collection | DOAJ |
| description | Malondialdehyde (MDA) engages in a triel bond (TrB) with TrX<sub>3</sub> (Tr = B and Al; X = H, F, Cl, and Br) in three modes, in which the hydroxyl O, carbonyl O, and central carbon atoms of MDA act as the electron donors, respectively. A H···X secondary interaction coexists with the TrB in the former two types of complexes. The carbonyl O forms a stronger TrB than the hydroxyl O, and both of them are better electron donors than the central carbon atom. The TrB formed by the hydroxyl O enhances the intramolecular H-bond in MDA and thus promotes proton transfer in MDA-BX<sub>3</sub> (X = Cl and Br) and MDA-AlX<sub>3</sub> (X = halogen), while a weakening H-bond and the inhibition of proton transfer are caused by the TrB formed by the carbonyl O. The TrB formed by the central carbon atom imposes little influence on the H-bond. The BH<sub>2</sub> substitution on the central C-H bond can also realise the proton transfer in the triel-bonded complexes between the hydroxyl O and TrH<sub>3</sub> (Tr = B and Al). |
| first_indexed | 2024-03-09T23:00:33Z |
| format | Article |
| id | doaj.art-f1fcad29b04c4c0a94face33fa55c36e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:00:33Z |
| publishDate | 2022-09-01 |
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| series | Molecules |
| spelling | doaj.art-f1fcad29b04c4c0a94face33fa55c36e2023-11-23T18:04:06ZengMDPI AGMolecules1420-30492022-09-012718609110.3390/molecules27186091Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton TransferQiaozhuo Wu0Shubin Yang1Qingzhong Li2The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, ChinaThe Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, ChinaThe Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, ChinaMalondialdehyde (MDA) engages in a triel bond (TrB) with TrX<sub>3</sub> (Tr = B and Al; X = H, F, Cl, and Br) in three modes, in which the hydroxyl O, carbonyl O, and central carbon atoms of MDA act as the electron donors, respectively. A H···X secondary interaction coexists with the TrB in the former two types of complexes. The carbonyl O forms a stronger TrB than the hydroxyl O, and both of them are better electron donors than the central carbon atom. The TrB formed by the hydroxyl O enhances the intramolecular H-bond in MDA and thus promotes proton transfer in MDA-BX<sub>3</sub> (X = Cl and Br) and MDA-AlX<sub>3</sub> (X = halogen), while a weakening H-bond and the inhibition of proton transfer are caused by the TrB formed by the carbonyl O. The TrB formed by the central carbon atom imposes little influence on the H-bond. The BH<sub>2</sub> substitution on the central C-H bond can also realise the proton transfer in the triel-bonded complexes between the hydroxyl O and TrH<sub>3</sub> (Tr = B and Al).https://www.mdpi.com/1420-3049/27/18/6091triel bondhydrogen bondingproton transferNBO |
| spellingShingle | Qiaozhuo Wu Shubin Yang Qingzhong Li Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer Molecules triel bond hydrogen bonding proton transfer NBO |
| title | Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer |
| title_full | Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer |
| title_fullStr | Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer |
| title_full_unstemmed | Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer |
| title_short | Triel Bond Formed by Malondialdehyde and Its Influence on the Intramolecular H-Bond and Proton Transfer |
| title_sort | triel bond formed by malondialdehyde and its influence on the intramolecular h bond and proton transfer |
| topic | triel bond hydrogen bonding proton transfer NBO |
| url | https://www.mdpi.com/1420-3049/27/18/6091 |
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