Computational study on fused five membered heterocyclic compounds containing tertiary oxygen
| Autor: | Shiru Jia, Tongcun Zhang, Huixin He, Yingai Piao, Liming Zhang, Xiuli Zhang, Yanying Hu, Yujie Dai |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Pentalene
010405 organic chemistry Stereochemistry Orbital hybridisation Organic Chemistry Aromaticity 010402 general chemistry 01 natural sciences Bond order 0104 chemical sciences Analytical Chemistry Inorganic Chemistry Bond length chemistry.chemical_compound Crystallography chemistry Molecule Molecular orbital Spectroscopy Natural bond orbital |
| Zdroj: | Journal of Molecular Structure. 1129:98-104 |
| ISSN: | 0022-2860 |
| Popis: | The structure, stability and electronic properties of two fused five membered heterocyclic compounds containing tertiary oxygen have been investigated with quantum chemistry computation. The results show that 3 H -4λ 3 -furo[1,2- a ]furan (M1) and 2a 1 λ 4 -oxacyclopenta[ cd ]pentalene (M2) both own three C O bonds and especially in M2 the three C O bonds and angles are approximately identical. The two compounds are comparatively stable and M2 with three pentacycles is more stable than compound M1 according to the C O bond lengths, bond orders, Egap, electronegativity ( χ ), hardness ( η ), electrophilicity ( ω ), and aromaticity indexes. The aromaticity indexes such as NICS(0), NICS(1) and NICS(1)zz show that they both have strong aromaticity. The natural bonding orbital (NBO) analysis shows that oxygen atom takes hybrid orbitals composed of s and p orbital components to form σ (C O) bonds in compounds M1 and M2. The second order perturbation analysis shows that the occurrence of intramolecular charge transfer within the molecule exists in compound M1. |
| Databáze: | OpenAIRE |
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