The conformational distribution of methyl phenyl sulfoxide (a molecule representative of a very important class of reagents widely used in asymmetric synthesis) has been studied in two different phases of matter (gas phase and solution) by a comprehensive approach including theoretical calculations, microwave spectroscopy, liquid crystal NMR experiments, and atomistic molecular dynamics computer simulations. The aim was to investigate the combined action of intra- and intermolecular interactions in determining the molecule’s conformational equilibrium, upon which important physicochemical properties (inter alia, the chemoselectivity) significantly depend. Basically, the results converge in describing the tendency of the molecule to favor stable conformations governed by intramolecular interactions (in particular, the expected optimization between steric repulsion and conjugation of ð systems). However, significant solvent effects (whose “absolute” magnitude is actually difficult to assess, due to a certain “method-dependence” of the results) have been also detected.

Celebre G., Cinacchi G., De Luca G., Giuliano B.M., Iemma F., Melandri S. (2008). Multitechnique investigation of conformational features of small molecules: The case of methyl phenyl sulfoxide. JOURNAL OF PHYSICAL CHEMISTRY. B, CONDENSED MATTER, MATERIALS, SURFACES, INTERFACES & BIOPHYSICAL, 112, 2095-2101 [10.1021/jp076969s].

Multitechnique investigation of conformational features of small molecules: The case of methyl phenyl sulfoxide

GIULIANO, BARBARA MICHELA;MELANDRI, SONIA
2008

Abstract

The conformational distribution of methyl phenyl sulfoxide (a molecule representative of a very important class of reagents widely used in asymmetric synthesis) has been studied in two different phases of matter (gas phase and solution) by a comprehensive approach including theoretical calculations, microwave spectroscopy, liquid crystal NMR experiments, and atomistic molecular dynamics computer simulations. The aim was to investigate the combined action of intra- and intermolecular interactions in determining the molecule’s conformational equilibrium, upon which important physicochemical properties (inter alia, the chemoselectivity) significantly depend. Basically, the results converge in describing the tendency of the molecule to favor stable conformations governed by intramolecular interactions (in particular, the expected optimization between steric repulsion and conjugation of ð systems). However, significant solvent effects (whose “absolute” magnitude is actually difficult to assess, due to a certain “method-dependence” of the results) have been also detected.
2008
Celebre G., Cinacchi G., De Luca G., Giuliano B.M., Iemma F., Melandri S. (2008). Multitechnique investigation of conformational features of small molecules: The case of methyl phenyl sulfoxide. JOURNAL OF PHYSICAL CHEMISTRY. B, CONDENSED MATTER, MATERIALS, SURFACES, INTERFACES & BIOPHYSICAL, 112, 2095-2101 [10.1021/jp076969s].
Celebre G.; Cinacchi G.; De Luca G.; Giuliano B.M.; Iemma F.; Melandri S.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/70779
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