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Structures of Tris(donor)-Tris(acceptor)-Substituted Benzenes, 1. Steric, Polar and Hydrogen-Bonding Effects in Triaminotrinitrobenzenes

✍ Scribed by Jens Wolff, J. ;Nelsen, Stephen F. ;Petillo, Peter A. ;Powell, Douglas R.

Publisher: Wiley (John Wiley & Sons)
Year: 1991
Tongue: English
Weight: 698 KB
Volume: 124
Category: Article
ISSN: 0009-2940
DOI: 10.1002/cber.19911240809

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✦ Synopsis

Conformational analysis / "Push-pull" interaction / Benzene ring, deformation to boat and twist-boat forms /

Calculations, AM1

The X-ray analyses of three 1,3,5-tris(alkylamino)-2,4,6-trinitrobenzenes (alkyl = iPr, neopentyl, t B u 1 df) show their benzene rings to be highly distorted towards boat ( l d .

iPrNHZ) and twist-boat (le,f) forms. The patterns found for intramolecular donor-acceptor interaction and hydrogen bonding depend on the conformation of the benzene core: boat structures have the "stern" amino group strongly donating to the "bow" nitro group in the para position and two stronger hydrogen bonds between the substituents on the "side" of the boat, whereas twist-boat structures have two amino groups ~

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