The plausible aromaticity of 1,8-naphthalimides: The enthalpy of formationof N-methyl-1,8-naphthalimide

Authors
Roux, MV Jimenez, P Davalos, JZ Martin-Luengo, MA Rotello, VM Cuello, AO Liebman, JF
Citation
Mv. Roux et al., The plausible aromaticity of 1,8-naphthalimides: The enthalpy of formationof N-methyl-1,8-naphthalimide, STRUCT CHEM, 11(1), 2000, pp. 1-7
Citations number
23
Categorie Soggetti
Chemistry
Journal title
STRUCTURAL CHEMISTRY
ISSN journal
10400400 → ACNP
Volume
11
Issue
1
Year of publication
2000
Pages
1 - 7
Database
ISI
SICI code
1040-0400(200002)11:1<1:TPAO1T>2.0.ZU;2-R
Abstract
In order to understand the aromaticity of 1,8-naphthalimides, the enthalpie s of combustion and sublimation of N-methyl-1,8-naphthalimide were determin ed. The numerical values are -6095.8 +/- 3.5 and 109.7 +/- 0.8 kJ . mol(-1) . The enthalpies of formation of condensed and gas phase N-methyl-1,8-napht halimide are accordingly -306.1 +/- 3.9 and -196.4 +/- 4.0 kJ . mol(-1). It is deduced that naphthalimides enjoy some 40 kJ . mol(-1) of aromatic stab ilization over that of the maleimides, shown to be nominally destabilized a nd modestly antiaromatic in our recently published thermochemical study.