DFT analysis of rotational barriers, 1H and 13C NMR chemical shifts in neutral and protonated furfurylidenanilines

Santos Carballal, David ORCID: https://orcid.org/0000-0002-3199-9588, Suardiaz, Reynier, Montero, Luis A. and Pérez, Carlos 2008. DFT analysis of rotational barriers, 1H and 13C NMR chemical shifts in neutral and protonated furfurylidenanilines. Journal of Molecular Structure THEOCHEM 852 (1-3) , pp. 78-82. 10.1016/j.theochem.2007.12.014

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Abstract

Rotational barriers were calculated for 4′-substituted neutral and protonated furfurylidenanilines (FA) by DFT methods and the corresponding equilibrium geometries were identified. Neutral FA have equilibrium dihedral angle values sensitive to the substituent. 1H and 13C Substituent Induced Shifts in FA were calculated from shielding tensors and compared with experimental ones. The experimental trends in 1H and 13C Substituent Induced Shifts of these compounds are well reproduced by the calculations. Differences in Mulliken charges for each position in neutral and protonated furfurylidenanilines were correlated with experimental 1H and 13C Substituent Induced Shifts. The experimental trends in 1H and 13C Substituent Induced Shifts were well reproduced by charge differences. Only the functional group 1H shifts do not correlate with the charges reflecting the variable effect of the anisotropy term due to the benzene ring. Protonation of FA removes this variability.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Elsevier
ISSN:	0166-1280
Last Modified:	28 Oct 2022 08:50
URI:	https://orca.cardiff.ac.uk/id/eprint/72365

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