| Hydride, hydrogen, proton, and electron affinities of imines and their reaction intermediates in acetonitrile and construction of thermodynamic characteristic graphs (TCGs) of imines as a "molecule ID card". | |
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MedLine Citation:
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PMID: 20043633 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C=N pi-bond in the imines were estimated. The polarity of the C=N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient "Molecule ID Card" was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines. |
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Authors:
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Xiao-Qing Zhu; Qiao-Yun Liu; Qiang Chen; Lian-Rui Mei |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Feb |
Date Detail:
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Created Date: 2010-01-29 Completed Date: 2010-04-05 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 789-808 Citation Subset: IM |
Affiliation:
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State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, China. xqzhu@nankai.edu.cn |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acetonitriles
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chemistry* Electrochemistry Electrons Hydrogen / chemistry* Imines / chemistry* Models, Molecular Molecular Structure Protons Thermodynamics |
| Chemical | |
Reg. No./Substance:
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0/Acetonitriles; 0/Imines; 0/Protons; 1333-74-0/Hydrogen; 75-05-8/acetonitrile |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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