Gas phase basicities of polyfunctional molecules. Part 5: Non-aromatic sp2 nitrogen containing compounds
| Autor: | Guy Bouchoux, Mirjana Eckert-Maksic |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Protonation Conjugated system 010402 general chemistry Condensed Matter Physics Mass spectrometry 01 natural sciences Quantum chemistry General Biochemistry Genetics and Molecular Biology 0104 chemical sciences Analytical Chemistry chemistry.chemical_compound chemistry Computational chemistry Thermochemistry Molecule Organic chemistry Lone pair Spectroscopy Phosphazene |
| Zdroj: | Mass Spectrometry Reviews. 37:139-170 |
| ISSN: | 0277-7037 |
| Popis: | This paper constitutes the fifth part of a general review of the gas-phase protonation thermochemistry of polyfunctional molecules (Part 1: Theory and methods, Mass Spectrom Rev 2007, 26:775-835, Part 2: Saturated basic sites, Mass Spectrom Rev 2012, 31:353-390, Part 3: Amino acids, Mass Spectrom Rev 2012, 31:391-435, Part 4: Carbonyl as basic site, Mass Spectrom Rev 2015, 34:493-534). This part is devoted to non-aromatic molecules characterized by a lone pair located on a sp2 nitrogen atom, it embraces functional groups such as imines, amidines, guanidines, diazenes, hydrazines, oximes, and phosphazenes. Specific examples are examined under five major chapters. In the first one, aliphatic and unsaturated (conjugated and cyclic) imines, hydrazones, and oximes are considered. A second chapter describes the protonation energetic of aliphatic, conjugated, or cyclic amidines. Guanidines, polyguanides, and biomolecules containing guanidine were examined in the third chapter. A fourth chapter describes the particular case of the phosphazene molecules. Finally, diazenes and azides were considered in the last chapter. Experimental data were re-evaluated according to the presently adopted basicity scale, i.e., PA(NH3 ) = 853.6 kJ/mol, GB (NH3 ) = 819 kJ/mol. Structural and energetic information given by G4MP2 quantum chemistry computations on typical systems are presented. © 2016 Wiley Periodicals, Inc. Mass Spec Rev 37:139-170, 2018. |
| Databáze: | OpenAIRE |
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