Electronegativity and resonance parameters from the geometry of monosubstituted benzene rings
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| Název: | Electronegativity and resonance parameters from the geometry of monosubstituted benzene rings |
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| Autoři: | CAMPANELLI, Anna Rita, Aldo Domenicano, Marina Macchiagodena, Fabio Ramondo |
| Zdroj: | Structural Chemistry. 22:1131-1141 |
| Informace o vydavateli: | Springer Science and Business Media LLC, 2011. |
| Rok vydání: | 2011 |
| Témata: | benzene ring geometry, electronegativity effect, monosubstituted benzene derivatives, resonance effect, small structural differences, steric effect, Monosubstituted benzene derivatives, Benzene ring geometry, Small structural differences, 01 natural sciences, 0104 chemical sciences |
| Popis: | Reference values of the structural substituent parameters, SE and SR, measuring the electronegativity and resonance effects, respectively, of functional groups (Campanelli et al. J Phys Chem A 107:6429–6440, 2003) have been determined from the benzene ring geometries of 100 Ph–X species, including different conformations of the same molecule. Geometries have been obtained by quantum chemical calculations at the HF/6-31G*, HF/6-311++G**, and B3LYP/6-311++G** levels of theory. The substituent parameters from HF/6-311++G** calculations are in close agreement with those determined at the HF/6-31G* level. Using the B3LYP density functional yields SE and SR values which—in general—correlate well with the corresponding HF values. Exceptions occur with some charged groups, and, in the case of SE, with a few dipolar groups having very high or low electronegativities. SR values from B3LYP calculations are about 22% smaller than the corresponding HF values. The variations of the benzene ring geometry caused by electronegativity, resonance, and steric effects are illustrated in some detail. |
| Druh dokumentu: | Article |
| Jazyk: | English |
| ISSN: | 1572-9001 1040-0400 |
| DOI: | 10.1007/s11224-011-9806-z |
| Přístupová URL adresa: | https://link.springer.com/article/10.1007%2Fs11224-011-9806-z https://link.springer.com/article/10.1007/s11224-011-9806-z/fulltext.html http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=000296322700021&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=0c7ff228ccbaaa74236f48834a34396a https://doi.org/10.1007/s11224-011-9806-z https://hdl.handle.net/11573/378303 https://hdl.handle.net/11697/20232 |
| Rights: | Springer TDM |
| Přístupové číslo: | edsair.doi.dedup.....0cf34dde11c600a56a377174dc95e17c |
| Databáze: | OpenAIRE |
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Nájsť tento článok vo Web of Science | Abstrakt: | Reference values of the structural substituent parameters, SE and SR, measuring the electronegativity and resonance effects, respectively, of functional groups (Campanelli et al. J Phys Chem A 107:6429–6440, 2003) have been determined from the benzene ring geometries of 100 Ph–X species, including different conformations of the same molecule. Geometries have been obtained by quantum chemical calculations at the HF/6-31G*, HF/6-311++G**, and B3LYP/6-311++G** levels of theory. The substituent parameters from HF/6-311++G** calculations are in close agreement with those determined at the HF/6-31G* level. Using the B3LYP density functional yields SE and SR values which—in general—correlate well with the corresponding HF values. Exceptions occur with some charged groups, and, in the case of SE, with a few dipolar groups having very high or low electronegativities. SR values from B3LYP calculations are about 22% smaller than the corresponding HF values. The variations of the benzene ring geometry caused by electronegativity, resonance, and steric effects are illustrated in some detail. |
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| ISSN: | 15729001 10400400 |
| DOI: | 10.1007/s11224-011-9806-z |