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- W2186040694 abstract "2-Acylated 2,3,1-benzodiazaborines can display unusual structures and reactivities. The crystal structure analysis of the boron heterocycle obtained by condensing 2-formylphenylboronic acid and picolinohydrazide reveals it to be an N→B-chelated zwitterionic tetracycle (systematic name: 1-hydroxy-11-oxo-9,10,17λ 5 -triaza-1λ 4 -boratetracyclo[8.7.0.0 2,7 .0 12,17 ]heptadeca-3,5,7,12,14,16-hexaen-17-ylium-1-uide), C 13 H 10 BN 3 O 2 , produced by the intramolecular addition of the Lewis basic picolinoyl N atom of 1-hydroxy-2-(pyridin-2-ylcarbonyl)benzo[ d ][1,2,3]diazaborinine to the boron heterocycle B atom acting as a Lewis acid. Neither of the other two pyridinylcarbonyl isomers ( viz . nicotinoyl and isonicotinoyl) are able to adopt such a structure for geometric reasons. A favored yet reversible chelation equilibrium provides an explanation for the slow D 2 O exchange observed for the OH resonance in the 1 H NMR spectrum, as well as for its unusual upfield chemical shift. Deuterium exchange may take place solely in the minor open (unchelated) species present in solution." @default.
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- W2186040694 date "2015-11-26" @default.
- W2186040694 modified "2023-09-23" @default.
- W2186040694 title "A zwitterion produced by a strong intramolecular N→B interaction in 1-hydroxy-2-(pyridin-2-ylcarbonyl)benzo[<i>d</i>][1,2,3]diazaborinine" @default.
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- W2186040694 doi "https://doi.org/10.1107/s2053229615021841" @default.
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