Spectroscopic and theoretical studies on the aromaticity of pyrrol-2-yl-carbonyl conformers

被引：7

作者：

Dubis, Alina T. ^{[1
]}

Wojtulewski, Slawomir ^{[1
]}

Filipkowski, Karol ^{[1
]}

机构：

[1] Univ Bialystok, Inst Chem, PL-15399 Bialystok, Poland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2013年 / 1041卷

关键词：

Pyrrol-2-yl carbonyl conformers; pi-Electron delocalization; HOMA; NICS; DFT calculations; Vibrational spectroscopy; C-SUBSTITUTED PYRROLECARBALDEHYDES; INDEPENDENT CHEMICAL-SHIFTS; DENSITY-FUNCTIONAL THEORY; MOLECULAR-ORBITAL METHODS; AB-INITIO; PYRROLE DERIVATIVES; BASIS-SETS; PART II; INDEX; DELOCALIZATION;

D O I：

10.1016/j.molstruc.2013.02.030

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The aromaticity of s-cis and s-trans pyrrol-2-yl carbonyl conformers was studied by FT-IR, H-1 NMR spectroscopy and DFT calculations at the B3LYP/6-311++G(d,p) level of theory. The Harmonic Oscillator Model of Aromaticity (HOMA) and Nucleus Independent Chemical Shift (NICS) indices were calculated to estimate pi-electron delocalization in the pyrrole ring. The usefulness of infrared spectroscopy in the evaluation of the aromaticity of the homogeneous set of pyrroles is discussed. The influence of 2-substitution on different aspects of aromaticity and stability of the pyrrol-2-yl carbonyl conformers is also discussed. It is concluded that the substitution effect of the title pyrrole derivatives can be explained on the basis of theoretical and experimental measurements of pi-electron delocalization, including IR data. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：92 / 99

页数：8

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