Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

Abstract

The title compound is the first example of a naphtho­quinone imine derivative crystallizing in the 4-imine/2-amine tautomeric form having bulky tert-butyl substituents at the N atoms.

Crystal structure of 4-[(adamantan-1-yl)amino]naphthalene-1,2-dione

“…1), the C O bond length of the carbonyl group at the 1-position [C11 O2 = 1.216 (2) Å ] is shorter than the other at the 2-position [C2 O1 = 1.241 (2) Å ], suggesting strong delocalization from the trigonal-planar nitrogen at the 4-position, causing a decrease of the double-bond character at the C2 carbonyl (vinylogous amide), whereas the C1 carbonyl atom is unaffected. Further evidence of this delocalization is shown by a short N1-C4 bond distance [1.346 (2) Å ], which is intermediate between the C-N and C N bond distances observed in a related quinone amine/imine structure (Lamoureux et al, 2018). The aliphatic bond distance [N1-C12 = 1.482 (2) Å ] is longer than expected, but may be caused by the bulky adamantanyl group.…”