Basicity of the polydentate captodative aminoenones. Ab initio, DFT, and FTIR study

被引：2

作者：

Kondrashov, E. V. ^{[1
]}

Oznobikhina, L. P. ^{[1
]}

Aksamentova, T. N. ^{[1
]}

Chipanina, N. N. ^{[1
]}

Romanov, A. R. ^{[1
]}

Rulev, A. Yu ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Inst Chem, 1 Favorsky St, Irkutsk 664033, Russia

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2016年 / 29卷 / 06期

关键词：

captodative aminoenones; DFT/MP2/IR study; homodesmotic reactions; hydrogen bond; NBO analysis; proton affinity; VINYLOGOUS GUANIDINIUM SALTS; INTRAMOLECULAR HYDROGEN-BOND; FOURIER-TRANSFORM IR; GAS-PHASE BASICITIES; SECONDARY-AMINES; TRIFLUOROMETHYLATED ENAMINES; NUCLEOPHILIC-SUBSTITUTION; CONFORMATIONAL-ANALYSIS; PROTON AFFINITIES; NMR-SPECTROSCOPY;

D O I：

10.1002/poc.3532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electron donating ability of the oxygen, nitrogen, and carbon atoms of captodative aminoenones R'CH = C(NR2)EWG, EWG = CHO, C(O)Me, C(O)CF3, C(O)Ph was investigated using ab initio and Density Functional Theory (DFT) calculations, Natural Bond Orbital (NBO) analysis, and Fourier Transform InfraRed (FTIR) spectroscopy. The influence of both electron withdrawing group (EWG) and double bond substituents on the proton affinity of the basic centers, orbital interaction, as well as resonance stabilization energies between heteroatoms and double bonds are discussed. The results obtained are critically compared with the push-pull aminoenones. The comparison of experimental values Delta nu OH and theoretical values of H-bonding energy was used to determine the H-complex type of aminoenone with phenol and the H-bond strength. Copyright (C) 2016 John Wiley & Sons, Ltd.

引用

页码：288 / 298

页数：11

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