BOAT AND TWIST-BOAT STRUCTURES OF 2,4,6-TRIS(ISOPROPYLAMINO)-1,3,5-TRINITROBENZENE - CONFORMATIONAL CHANGE THROUGH INTERMOLECULAR HYDROGEN-BONDING | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7701196

Reference Type

Journal Article

Title

BOAT AND TWIST-BOAT STRUCTURES OF 2,4,6-TRIS(ISOPROPYLAMINO)-1,3,5-TRINITROBENZENE - CONFORMATIONAL CHANGE THROUGH INTERMOLECULAR HYDROGEN-BONDING

Author(s)

Wolff, JJ; Nelsen, SF; Powell, DR; ,

Year

1991

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Page Numbers

5908-5911

Web of Science Id

WOS:A1991GH36900037

Abstract

2,4,6-Tris(isopropylamino)-1,3,5-trinitrobenzene (2a) cocrystallizes with isopropylamine in a highly distorted boat form (2a1) but adopts an almost equally distorted twist-boat from (2a2) in a cocrystal with toluene. In the boat from, a quinonoid resonance pattern is found for the benzene core, whereas no such simple resonance equivalent exists for the twist-boat form. Differences in the donor-acceptor relationships between 2a1 and 2a2 are discussed in terms of bond lengths and are substantiated by UV-vis spectroscopy: the band at longest wavelengths in the solid-state UV-vis spectrum of 2a1 is shifted by 27 +/- 7 nm in comparison to that of 2a2, a difference of 5.8 +/- 1.5 kcal/mol in energy. For solutions of 2a, UV-vis indicates the presence of both conformers in different amounts that vary with temperature.