Synthesis and Characterization of Stable Phosphorus Carbabetaines

Chemistry, an Asian Journal
Hikaru YanaiTakashi Matsumoto

Abstract

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.

References

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Aug 2, 2012·Chemical Communications : Chem Comm·Hikaru Yanai, Takeo Taguchi
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Sep 21, 2013·Chemical Communications : Chem Comm·Hikaru YanaiTakashi Matsumoto
Jan 27, 2015·Chemical Communications : Chem Comm·Benito AlcaideCarlos Lázaro-Milla
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Jan 7, 2016·Chemical Communications : Chem Comm·Hikaru YanaiTakashi Matsumoto
May 28, 2016·Chemistry : a European Journal·Benito AlcaideCarlos Lázaro-Milla

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Citations

Apr 27, 2019·Angewandte Chemie·Hikaru YanaiTakashi Matsumoto
Sep 21, 2021·Chemistry : a European Journal·Shoki HoshikawaTakashi Matsumoto

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