The configurational and conformational properties of six 4-trimethylammoniummethyl 2,2-disubstituted 1,3-dioxolanes were studied using NOE experiments and vicinal coupling constants. Selective 1D NOE experiments proved to be effective tools in the configurational assignment of C-2 relative to C-4, The preferred conformation of the dioxolane ring and the exocyclic group at C-4 was obtained by employing vicinal coupling constants and NOE results. The H-1 and C-13 NMR chemical shifts show stereochemically dependent trends, Quantitative analysis of conformer populations was performed using Haasnoot et al's equation. The -N+(CH3)(3) group was found to be synclinal with respect to the heterocyclic 0-3 atom and points outside the ring, When a phenyl group is present at C-2, the 4-CH2N+ - group in a trans relationship to the 2-phenyl ring was found to occur prevalently in a pseudo-axial orientation, whereas it was established to be prevalently pseudo-equatorial when cis with respect to the phenyl ring.

CONFORMATIONAL AND CONFIGURATIONAL STUDY OF 1,3-DIOXOLANES BY PROTON AND CARBON NMR-SPECTROSCOPY / Mucci, Adele; Schenetti, Luisa; Brasili, Livio; Malmusi, L.. - In: MAGNETIC RESONANCE IN CHEMISTRY. - ISSN 0749-1581. - STAMPA. - 33:(1995), pp. 167-173.

CONFORMATIONAL AND CONFIGURATIONAL STUDY OF 1,3-DIOXOLANES BY PROTON AND CARBON NMR-SPECTROSCOPY

MUCCI, Adele;SCHENETTI, Luisa;BRASILI, Livio;
1995

Abstract

The configurational and conformational properties of six 4-trimethylammoniummethyl 2,2-disubstituted 1,3-dioxolanes were studied using NOE experiments and vicinal coupling constants. Selective 1D NOE experiments proved to be effective tools in the configurational assignment of C-2 relative to C-4, The preferred conformation of the dioxolane ring and the exocyclic group at C-4 was obtained by employing vicinal coupling constants and NOE results. The H-1 and C-13 NMR chemical shifts show stereochemically dependent trends, Quantitative analysis of conformer populations was performed using Haasnoot et al's equation. The -N+(CH3)(3) group was found to be synclinal with respect to the heterocyclic 0-3 atom and points outside the ring, When a phenyl group is present at C-2, the 4-CH2N+ - group in a trans relationship to the 2-phenyl ring was found to occur prevalently in a pseudo-axial orientation, whereas it was established to be prevalently pseudo-equatorial when cis with respect to the phenyl ring.
1995
33
167
173
CONFORMATIONAL AND CONFIGURATIONAL STUDY OF 1,3-DIOXOLANES BY PROTON AND CARBON NMR-SPECTROSCOPY / Mucci, Adele; Schenetti, Luisa; Brasili, Livio; Malmusi, L.. - In: MAGNETIC RESONANCE IN CHEMISTRY. - ISSN 0749-1581. - STAMPA. - 33:(1995), pp. 167-173.
Mucci, Adele; Schenetti, Luisa; Brasili, Livio; Malmusi, L.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/10256
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