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Benzo[ c ]benzo[3,4]cinnolino[1,2‐ a ]cinnoline, a Chiral Hydrazine Derivative
Author(s) -
Fischer Hans,
Krieger Claus,
Neugebauer Franz A.
Publication year - 1986
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.198603741
Subject(s) - cinnoline , racemization , vicinal , chemistry , enantiomer , lone pair , derivative (finance) , stereochemistry , crystallography , hydrazine (antidepressant) , medicinal chemistry , molecule , organic chemistry , chromatography , financial economics , economics
The spontaneous crystallization of the enantiomers of the title compound 1 (space group P 2 1 ) has been observed. The X‐ray structure analysis reveals a pyramidal arrangement of the substituents on the nitrogen atoms. The large barrier to racemization (27.1 kcal mol −1 ) is largely due to the gauche effect of the vicinal lone pairs of electrons.