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Hydrogen Bonds between an NH 4 ⊕ Ion and a Carbanion—Crystal Structure of Ammonium 1,2,4‐Tricyanocyclopentadienide
Author(s) -
Buchholz Stefan,
Harms Klaus,
Massa Werner,
Boche Gernot
Publication year - 1989
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.198900731
Subject(s) - carbanion , nitrile , hydrogen bond , chemistry , crystal structure , ion , crystallography , derivative (finance) , crystal (programming language) , stereochemistry , molecule , organic chemistry , computer science , financial economics , programming language , economics
The H 3 N ⊕ H ⃛C hydrogen bond found for the first time in the crystalline state is consistent with concepts developed by Cram for the mechanism of the D/H exchange which proceeds with unusually high retention ( k A / k rac = 148) on reaction of a fluorenyl derivative with NH 3 . Each nitrile N atom of the title compound is bound via an H bond to an NH 4 ⊕ion, and each NH 4 ⊕ion forms three H bonds to nitrile N atoms and one hydrogen bond to a cyclopentadienide C atom. The picture on the right shows a section of the crystal structure (in hydrogen bond).