| Infrared and theoretical calculations in 2-halocycloheptanones conformational analysis. | |
| | |
MedLine Citation:
|
PMID: 22534556 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
2-Halocycloheptanones (Halo=F, Cl, Br and I) were synthesized and their conformational analysis was performed through infrared spectroscopy data. The corresponding conformers geometries and energies were obtained by theoretical calculations at B3LYP/aug-cc-pVDZ level of theory in the isolated state and in solution. It was observed, by both approaches, that the conformational preferences were very sensitive to the solvent polarity, since its increase led to an increase in the population of the more polar conformer. An analysis of these conformational equilibria showed they suffer also the influence of stereoelectronic effects, like hyperconjugation and steric effects. These results were interpreted using natural bond orbital (NBO) analysis, which indicated that the electronic delocalization to the orbital π*(CO) is directly involved in the stability increase of conformers I and II. The relative effect of the period of the halogen can also be noted, with changes in the conformational preferences and in the energies involved in the interactions of NBO. |
| | |
Authors:
|
Thiago C Rozada; Gisele F Gauze; Denize C Favaro; Roberto Rittner; Ernani A Basso |
Related Documents
:
|
15556426 - Determination of the overlapping pka values of resorcinol using uv-visible spectroscopy... 11749636 - Absolute configurations, predominant conformations, and tautomeric structures of enanti... 20372746 - Extending the reliability and applicability of b3lyp. 11798306 - Conformational studies on 1,2-di- and 1,2,3-trisubstituted heterocycles. a spectroscopi... 17911246 - Adaptations of guest and host in expanded self-assembled capsules. 16530786 - Cytoplasmic shuttling of protons in anabaena sensory rhodopsin: implications for signal... |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2012-3-21 |
Journal Detail:
|
Title: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Volume: 94C ISSN: 1873-3557 ISO Abbreviation: - Publication Date: 2012 Mar |
Date Detail:
|
Created Date: 2012-4-26 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 9602533 Medline TA: Spectrochim Acta A Mol Biomol Spectrosc Country: - |
Other Details:
|
Languages: ENG Pagination: 277-287 Citation Subset: - |
Copyright Information:
|
Copyright © 2012 Elsevier B.V. All rights reserved. |
Affiliation:
|
Departamento de Química, Universidade Estadual de Maringá, Av. Colombo, 5790, 87020-900 Maringá, PR, Brazil. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Risk of contrast induced nephropathy in the critically ill: a prospective, case matched study.
Next Document: Spectroscopic analysis (FT-IR/FT-Raman) and molecular structure investigation on m-fluoronitrobenzen...