A refinement of the benzoic acid structure at room temperature

Abstract

Abstract. C7H602, monoclinic,

4-(Acetylamino)-3-hydroxy-5-nitrobenzoic Acid

“…However, further details concerning the conformation of the carboxyl, Nacetyl and nitro substituents of the title compound were needed for the purpose of further characterization. The benzene ring atoms are planar to within 0.026(2)A, with C--C bond lengths varying from 1.377 (3) to 1.408 (3)/~ and endocyclic C---C--C bond angles varying from 118.7(2) to 122.2(2) ° , which agrees with accepted values (Bruno & Randaccio, 1980;Karle, 1952a,b). The carboxyl, nitro and N-acetyl groups are rotated with respect to the benzene ring by 5.0 (3), 45.0 (2) and 37.3 (1) °, respectively.…”

“…This structure and those of similar compounds are of importance both for their application in structure-based drug design and in structure-activity studies of the influenza virus neuraminidase protein (Jedrzejas et al, 1995). The structure of benzoic acid has been well established by both X-ray and neutron studies (Sim, Robertson & Goodwin, 1955;Bruno & Randaccio, 1980;Feld, Lehman, Muir & Speakman, 1981). However, further details concerning the conformation of the carboxyl, Nacetyl and nitro substituents of the title compound were needed for the purpose of further characterization.…”

Structural studies of benzene derivatives. X. Refinement of the structure of p-chlorobenzoic acid

“…They consist of: (i) a lengthening (by 0.009-0.010 A, 5a) of the C(1)-C(2) and C(1)-C(6) bonds with respect to the central C-C bonds of the ring; (ii) an increase from 120 ° (by 2.0 °, 12a) of the C(3)-C(4)-C(5) angle, ao; and (iii) a decrease from 120 ° (by 1.2 °, To) of the C(2)-C(3)-C(4) and C(4)-C(5)-C(6) angles, fla. Since the COOH group is known to cause only minor changes of the ring angles (Domenicano & Murray-Rust, 1979;Bruno & Randaccio, 1980), the angular distortions occurring in p-chlorobenzoic acid should be attributed primarily to the C1 substituent. Indeed the value of aa, 122.0 (2) °, is close to the values obtained for the corresponding parameter in a variety of para-and meta-substituted derivatives of chlorobenzene, X-C6H4-CI, where the angular changes caused by the X substituent in the para or meta positions of the ring are known (or expected, on the basis of the nature and electronic properties of X) to be at most a few tenths of a degree (Table 6).…”

Theoretical Study of Multidimensional Proton Tunnelling in Benzoic Acid Dimer

“…It is present in the structure of the crystal [26][27][28]. Its proton transfer has been recently studied by inelastic neutron scattering by Plazanet et al [29] and Fillaux et al [30].…”