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Large Hyperconjugative and Inductive Effects on CCX Bond Angles (X = Main‐Group Element): The Crystal Structure of Triethylborane and Ab Initio Investigations
Author(s) -
Boese Roland,
Bläser Dieter,
Niederprüm Norbert,
Nüsse Markus,
Brett Waldemar A.,
von Ragué Schleyer Paul,
Bühl Michael,
van Eikema Hommes Nicolaas J. R.
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.199203141
Subject(s) - tetrahedron , triethylborane , group (periodic table) , boron , chemistry , ab initio , atomic orbital , crystallography , main group element , crystal structure , computational chemistry , ab initio quantum chemistry methods , molecular orbital , molecule , physics , transition metal , organic chemistry , quantum mechanics , electron , catalysis
Tetrahedral angles are the exception rather than the rule in compounds containing maingroup elements and organic groups. The deviations may be substantial as is demonstrated by the opening of the CCB angle in triethylborane to almost 120° (structure shown right), which can be explained by the hyperconjugative interaction of boron's empty p orbital with the bonding orbitals of the αCH bonds. This interpretation is supported by ab initio calculations and structural determinations of this and other compounds with the Et–X structural element (X = main‐group element).