Investigation of solute-solvent interactions in phenol compounds: accurate ab initio calculations of solvent effects on (1)H NMR chemical shifts
| dc.contributor.author | Siskos, M. G. | en |
| dc.contributor.author | Kontogianni, V. G. | en |
| dc.contributor.author | Tsiafoulis, C. G. | en |
| dc.contributor.author | Tzakos, A. G. | en |
| dc.contributor.author | Gerothanassis, I. P. | en |
| dc.date.accessioned | 2015-11-24T16:40:30Z | |
| dc.date.available | 2015-11-24T16:40:30Z | |
| dc.identifier.issn | 1477-0539 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/8285 | |
| dc.rights | Default Licence | - |
| dc.title | Investigation of solute-solvent interactions in phenol compounds: accurate ab initio calculations of solvent effects on (1)H NMR chemical shifts | en |
| heal.abstract | Accurate (1)H chemical shifts of the -OH groups of polyphenol compounds can be calculated, compared to experimental values, using a combination of DFT, polarizable continuum model (PCM) and discrete solute-solvent hydrogen bond interactions. The study focuses on three molecular solutes: phenol, 4-methylcatechol and the natural product genkwanin in DMSO, acetone, acetonitrile, and chloroform. Excellent linear correlation between experimental and computed chemical shifts (with the GIAO method at the DFT/B3LYP/6-311++G(2d,p) level) was obtained with minimization of the solvation complexes at the DFT/B3LYP/6-31+G(d) and DFT/B3LYP/6-311++G(d,p) level of theory with a correlation coefficient of 0.991. The use of the DFT/B3LYP/6-31+G(d) level of theory for minimization could provide an excellent means for the accurate prediction of the experimental OH chemical shift range of over 8 ppm due to: (i) strong intramolecular and solute-solvent intermolecular hydrogen bonds, (ii) flip-flop intramolecular hydrogen bonds, and (iii) conformational effects of substituents of genkwanin. The combined use of ab initio calculations and experimental (1)H chemical shifts of phenol -OH groups provides a method of primary interest in order to obtain detailed structural, conformation and electronic description of solute-solvent interactions at a molecular level. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | 10.1039/c3ob41556b | - |
| heal.identifier.secondary | http://www.ncbi.nlm.nih.gov/pubmed/24071830 | - |
| heal.identifier.secondary | http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob41556b | - |
| heal.journalName | Org Biomol Chem | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2013 | - |
| heal.publisher | Royal Society of Chemistry | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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