Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols

The 13C chemical shifts of nine 2-X-substituted phenetol derivatives were measured together with the 13C chemical shifts of the corresponding X-monosubstituted benzenes. Using an additivity scheme, the ethoxy cis-and trans-ortho-SCSs (substituent chemical shifts) at C-6 and C-2, respectively, were d...

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Autores principales: De Kowalewski, D.G., Kowalewski, V.J., Botek, E., Contreras, R.H., Facelli, J.C.
Formato: JOUR
Materias:
13c chemical shifts
13c nmr
Conformational effects
NMR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_07491581_v35_n6_p351_DeKowalewski
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_07491581_v35_n6_p351_DeKowalewski2023-10-03T15:39:24Z Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols De Kowalewski, D.G. Kowalewski, V.J. Botek, E. Contreras, R.H. Facelli, J.C. 13c chemical shifts 13c nmr Conformational effects NMR The 13C chemical shifts of nine 2-X-substituted phenetol derivatives were measured together with the 13C chemical shifts of the corresponding X-monosubstituted benzenes. Using an additivity scheme, the ethoxy cis-and trans-ortho-SCSs (substituent chemical shifts) at C-6 and C-2, respectively, were determined to be shielding effects of 16.5 and 10.9 ppm, respectively, which are close to those determined previously in anisole derivatives. Optimized geometries at the Hartree-Fock level employing a D95** basis set for three different phenetol conformers were obtained and the corresponding chemical shifts of all 13C nuclei were calculated using the same basis set and the CHF-GIAO approach. Results are discussed in terms of different interactions defining different conformations, particularly that between a polar bond and a proximate highly polarizable one. Fil:Kowalewski, V.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Botek, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Contreras, R.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Facelli, J.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_07491581_v35_n6_p351_DeKowalewski
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 13c chemical shifts
13c nmr
Conformational effects
NMR
spellingShingle 13c chemical shifts
13c nmr
Conformational effects
NMR
De Kowalewski, D.G.
Kowalewski, V.J.
Botek, E.
Contreras, R.H.
Facelli, J.C.
Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
topic_facet 13c chemical shifts
13c nmr
Conformational effects
NMR
description The 13C chemical shifts of nine 2-X-substituted phenetol derivatives were measured together with the 13C chemical shifts of the corresponding X-monosubstituted benzenes. Using an additivity scheme, the ethoxy cis-and trans-ortho-SCSs (substituent chemical shifts) at C-6 and C-2, respectively, were determined to be shielding effects of 16.5 and 10.9 ppm, respectively, which are close to those determined previously in anisole derivatives. Optimized geometries at the Hartree-Fock level employing a D95** basis set for three different phenetol conformers were obtained and the corresponding chemical shifts of all 13C nuclei were calculated using the same basis set and the CHF-GIAO approach. Results are discussed in terms of different interactions defining different conformations, particularly that between a polar bond and a proximate highly polarizable one.
format JOUR
author De Kowalewski, D.G.
Kowalewski, V.J.
Botek, E.
Contreras, R.H.
Facelli, J.C.
author_facet De Kowalewski, D.G.
Kowalewski, V.J.
Botek, E.
Contreras, R.H.
Facelli, J.C.
author_sort De Kowalewski, D.G.
title Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
title_short Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
title_full Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
title_fullStr Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
title_full_unstemmed Experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
title_sort experimental and theoretical study of the ethoxy group conformational effect on 13c chemical shifts in ortho-substituted phenetols
url http://hdl.handle.net/20.500.12110/paper_07491581_v35_n6_p351_DeKowalewski
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AT kowalewskivj experimentalandtheoreticalstudyoftheethoxygroupconformationaleffecton13cchemicalshiftsinorthosubstitutedphenetols
AT boteke experimentalandtheoreticalstudyoftheethoxygroupconformationaleffecton13cchemicalshiftsinorthosubstitutedphenetols
AT contrerasrh experimentalandtheoreticalstudyoftheethoxygroupconformationaleffecton13cchemicalshiftsinorthosubstitutedphenetols
AT facellijc experimentalandtheoreticalstudyoftheethoxygroupconformationaleffecton13cchemicalshiftsinorthosubstitutedphenetols
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