Issue 10, 1993
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Thermochemical and crystallographic studies of some β-ketoimine derivatives

Manuel A. V. Ribeiro Da Silva,   Maria D. M. C. Ribeiro Da Silva,   José P. A. Paiva,   Isabel M. C. S. Nogueira,   A. Margarida Damas,   James V. Berkley,   Marjorie M. Harding,   Margaret J. Akello  and  Geoffrey Pilcher  

Abstract

The standard (p°= 0.1 MPa) molar enthalpies of formation at 298.15 K in the gaseous state of some β-ketoimines, RCOCH[double bond, length half m-dash]C(CH3)NHR1, were determined from their enthalpies of combustion and of sublimation, ΔfH°m(g)/kJ mol–1: R[double bond, length half m-dash]CH3, {R1= C6H5, –66.0 ± 4.2; R1=p-C6H4NO2, –98.9 ± 5.0}: R = C6H5, {R1= H, –48.7 ± 3.5; R1= CH3, –53.7 ± 4.7; R1= C6H5, 69.1 ± 4.2}. From these results it is shown that the increase in delocalization energy from R = CH3 to R = C6H5 matches the corresponding increase between acetylacetone and benzoylacetone. Crystal structures are reported for R = CH3, R1=p-C6H4NO2, and R = C6H5{R1= H, R1= CH3}, and show that those β-ketoimines with R = C6H5 have a more delocalized structure in the –COCH[double bond, length half m-dash]C(CH3)NH–moiety than those with R = CH3 in accord with the thermochemical results.

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Article information

DOI
https://doi.org/10.1039/P29930001765
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1993, 1765-1769

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Thermochemical and crystallographic studies of some β-ketoimine derivatives

M. A. V. R. Da Silva, M. D. M. C. R. Da Silva, J. P. A. Paiva, I. M. C. S. Nogueira, A. M. Damas, J. V. Berkley, M. M. Harding, M. J. Akello and G. Pilcher, J. Chem. Soc., Perkin Trans. 2, 1993, 1765 DOI: 10.1039/P29930001765

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