Synthesis and Characterization of Stable Phosphorus Carbabetaines.

Autor: Yanai H; School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan., Almendros P; Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (IQOG-CSIC), Juan de la Cierva 3, 28006, Madrid, Spain., Takahashi S; School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan., Lázaro-Milla C; Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040, Madrid, Spain., Alcaide B; Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040, Madrid, Spain., Matsumoto T; School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2018 May 17. Date of Electronic Publication: 2018 May 17.
DOI: 10.1002/asia.201800769
Abstrakt: Phosphorus 1,3- and 1,4-carbabetaines with 'P(+)-C-C(-)' and 'P(+)-C-C-C(-)' structures, respectively, in which the carbanion moiety was significantly stabilized by two trifluoromethylsulfonyl groups, have been synthesized and characterized. Analysis of their X-ray crystal structures revealed that any attractive interactions between the anionic and cationic moieties were negligibly weak. This result was corroborated by using natural bond orbital (NBO) and Bader's quantum theory of atoms in molecules (QTAIM) models. In contrast, performing the same analysis of a known 1,3-carbabetaine equivalent, which can be drawn as a 'P(+)-C-C=C-O(-)' resonance structure, revealed pronounced charge-transfer interactions between the anionic and cationic moieties.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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