Equilibria between Nonclassical and Classical Boron Compounds, Competition between Aromaticity in Two and Three Dimensions | Zendy

Michel Holger | Zendy; Steiner Dirk | Zendy; Wočadlo Sigrid | Zendy; Allwohn Jürgen | Zendy; Stamatis Nicolaos | Zendy; Massa Werner | Zendy; Berndt Armin | Zendy

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Equilibria between Nonclassical and Classical Boron Compounds, Competition between Aromaticity in Two and Three Dimensions

Author(s) -

Michel Holger,

Steiner Dirk,

Wočadlo Sigrid,

Allwohn Jürgen,

Stamatis Nicolaos,

Massa Werner,

Berndt Armin

Publication year - 1992

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.199206071

Subject(s) - aromaticity , benzene , boron , ring (chemistry) , carborane , chemistry , chemical shift , computational chemistry , competition (biology) , thermodynamics , stereochemistry , organic chemistry , physics , molecule , ecology , biology

Carborane 1 and organoborane 2 are in equilibrium in solution. This is deduced from the temperature dependence of the position of the 11 B and 13 C NMR signals of 1 (R = t Bu or mesityl). An estimation of the thermodynamic parameters shows that the energy difference between 1 and 2 (1–2 kcal mol −1 ) is significantly less than for the parent compounds without a fused benzene ring (37.5 kcal mol −1 ). A possible explanation is that two‐dimensional aromaticity is lost in the transition from 2 to 1 .

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