1. Dynamic Conversion Between Se--N Covalent and Noncovalent Interactions.
- Author
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Meng Xie, Lili Wang, Fang Liu, Dongju Zhang, and Jun Gao
- Subjects
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COVALENT bonds , *TOXICOLOGICAL interactions , *DENSITY functional theory , *PYRIDINE , *CHEMICAL amplification - Abstract
Se--N dynamic covalent bond is a new dynamic covalent bond which has applications in the fabrication of stimuli responsive and self-healing functional materials. Although recent advances have been achieved in the experimental aspect, little is known about the formation mechanism of Se--N dynamic covalent bond. Here the structures and nature of Se--N dynamic covalent bond between three kinds of pyridine derivatives R-C5H4N, [pyridine (R = H), 4-methylpyridine (R = CH3), 4-dimethylamino-pyridine (R = N(CH3)2)] and phenylselenyl bromine (PhSeBr) have been analyzed using density functional theory. The interactions between Se atom in PhSeBr and N atom in pyridine or pyridine derivatives can be divided into three models: dissociation, nonbonding interaction and covalent bond interaction. Quantum chemical calculations on three series compounds show that these three models can convert mutually, which results in the generation of Se--N dynamic covalent bond. Solvent effects produced in polar solvents such as CH2Cl2 can make the conversion between Se--N covalent bond and Se...N nonbonding interactions easier. The kind of the substituents in pyridine ring can affect the conversion process: the stronger the electron-donating ability of the substituent, the easier the structure transformation. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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