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Dilithiation of a Primary Amine: Synthesis and Structure of [(α‐Naphthyl‐NLi 2 ) 10 (Et 2 O) 6 ] · Et 2 O, a Paramagnetic Li 20 Aggregate
Author(s) -
Armstrong David R.,
Barr Donald,
Clegg William,
Drake Simon R.,
Singer Richard J.,
Snaith Ronald,
Stalke Dietmar,
Wright Dominic S.
Publication year - 1991
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.199117071
Subject(s) - chemistry , deprotonation , paramagnetism , crystallography , amine gas treating , ab initio , cluster (spacecraft) , ether , primary (astronomy) , ion , organic chemistry , physics , condensed matter physics , computer science , astronomy , programming language
Ab initio calculations predict the stablest dilithiated α‐naphthylamine to be the isomer depeicted here. The C8 and N atoms are deprotonated and the two Li atoms occupy bridging positions between them. The reaction of α‐naphthylamine with n BuLi in ether at −40°C affords the title complex, whose structure is characterized by a central N 10 Li 14 cluster formed by two face‐sharing rhombic dodecahedrons. Amazingly the compound is paramagnetic in solution and in the solid.