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Thermally induced acyl migration in salicylamides. 1. Structures of the reactants, ${O}$-acetylsalicylamide and ${O}$-benzoylsalicylamide

Vyas, K and Rao, Mohan V and Manohar, H (1987) Thermally induced acyl migration in salicylamides. 1. Structures of the reactants, ${O}$-acetylsalicylamide and ${O}$-benzoylsalicylamide. In: Acta Crystallographica Section C, 43 (6). pp. 1197-1200.

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Abstract

${O}$ -Acetylsalicylamide (Ia), {C_9H_9NO_3}, {M_r} =179.18, monoclinic, {P2_1/c}, a=8.155(5), b=8.571 (2), c= 13.092 (3)A, \beta =99.54(5)° , V=902.4(6) {A^3} , Z=4, {D_m} =l.31, {D_x} =l.319 {gcm^-3}, {\lambda(M_o K \alpha)} = 0.71069 A, \mu = 1.08 {cm^-1}, F(000) = 376, T = 295 K, R = 0.076 for 1604 reflections. O-Benzoylsalicylamide (Ib), {C_{14}H_{11}NO_3}, {M_r}=241.2, monoclinic, {P2_1/c}, a=9.423(1), b=5.116(1), e=26.424 (2) A, \beta = 103.97 (1)% V= 1236.2 (3) {A^3}, Z= 4, {D_m} = 1.28, {D_x} = 1.296 {gcm^-3}, {\lambda (Cu K \alpha)} = 1.5418 A, \mu = 7.71 {cm^-1}, F(000) = 504, T= 295 K, R =0.050 for 2115 reflections. The dihedral angles between the amide group and the benzene ring are 39.9 ° (Ia) and 37.9 ° (Ib), whereas between the acyl group and the benzene ring they are 78.1 ° (Ia) and 93.4 ° (Ib). The differences in the packing of the two structures are brought out in terms of the observed hydrogen-bonding patterns. Based on the crystallographic results, an intramolecular mechanism for the migration of the acyl group from the O to the N position is suggested in both compounds.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to the International Union of Crystallography
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 09 May 2008
Last Modified: 19 Sep 2010 04:44
URI: http://eprints.iisc.ernet.in/id/eprint/13915

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