Carbene Analogues of Boron Stabilized by Neighboring BB Moieties: Doubly Aromatic Bishomotriboriranides | Zendy

Unverzagt Markus | Zendy; Subramanian Govindan | Zendy; Hofmann Matthias | Zendy; von Ragué Schleyer Paul | Zendy; Berger Stefan | Zendy; Harms Klaus | Zendy; Massa Werner | Zendy; Berndt Armin | Zendy

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Carbene Analogues of Boron Stabilized by Neighboring BB Moieties: Doubly Aromatic Bishomotriboriranides

Author(s) -

Unverzagt Markus,

Subramanian Govindan,

Hofmann Matthias,

von Ragué Schleyer Paul,

Berger Stefan,

Harms Klaus,

Massa Werner,

Berndt Armin

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199714691

Subject(s) - carbene , boron , aromaticity , delocalized electron , chemistry , electron delocalization , ion , crystallography , solid state , stereochemistry , medicinal chemistry , molecule , organic chemistry , catalysis

Delocalization in doubly aromatic compounds: Bishomotriboriranide 1 is the first carbene analogue of boron (a borenate ion) characterized in solution (NMR) and in the solid state (X‐ray). With the 3c–2e π bond and 3c–2e π bond that involves the borenate center of 1 * and the neighboring BB unit, 1 belongs to the class of doubly aromatic compounds. The (hypothetical) classical borenate 1 * without these delocalizations is estimated to be about 90 kcal mol −1 higher in energy than 1 (Dur = 2,3,5,6‐tetramethylphenyl).

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