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Covalent Hypercoordination: Can Carbon Bind Five Methyl Ligands?
Author(s) -
McKee William C.,
Agarwal Jay,
Schaefer Henry F.,
Schleyer Paul von R.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403314
Subject(s) - covalent bond , carbon atom , dissociation (chemistry) , chemistry , denticity , carbon fibers , atom (system on chip) , stereochemistry , crystallography , materials science , organic chemistry , crystal structure , computer science , alkyl , composite number , embedded system , composite material
C(CH 3 ) 5 + is the first reported example of a five‐coordinate carbon atom bound only to separate (that is, monodentate) carbon ligands. This species illustrate the limits of carbon bonding, exhibiting Lewis‐violating “electron‐deficient bonds” between the hypercoordinate carbon and its methyl groups. Though not kinetically persistent under standard laboratory conditions, its dissociation activation barriers may permit C(CH3) 5 + fleeting existence near 0 K.