The Crystal and Molecular Structure of Benzanilide

Abstract

The crystal structure of benzanilide has been determined from Weissenberg photographs using Cu Kα radiations and refined to an R value of 0.075 for 766 independent reflections. The crystals are monoclinic, space group C2/c, Z=4, with a=24.34(4), b=5.325(3), c=8.012(8) Å, β=107.2(3)°, Dm=1.32 and Dx=1.321 g cm−3. Dihedral angle between the benzene rings is 62.6°, and each benzene ring makes dihedral angle of 31.3 and 31.6° with the plane of amido group as found in Kevlar and Nomex polymers. The molecules related by a b-translation are linked together by N–H…O hydrogen bond [N…O 3.112(6), H…O 2.03 Å, N–H…O 157°] to form a chain along b. The chains are held together primarily by dipole forces of carbonyl groups of the molecules related by inversion centers to form a sheet parallel to the bc plane. The sheets are stacked along a with disorder by van der Waals interactions.

Syntheses and X‐Ray Structures for Model Compounds of a Pyrimidinediyl‐Based Rigid‐Rod Aromatic Polyamide

“…Interplanar angles between the amide groups and the pyrimidinyl and phenylene rings are given in Table 2. The dihedral angles for 3 (see Table 2) are comparable with those for benzanilide [8] (29.4, 37.3, and 62.6", resp.). However, the intermolecular interactions are different in these two crystal structures: the benzanilide molecules are linked by NH .…”

“…3 that the small dihedral angle between the amide group and the pyrimidinyl ring is mainly caused by the Ni-O(9) and NiGN(1) bonds. It is not possible, however, to determine whether special packing features of the crystal structure of 4 or more general resonance effects (as discussed in [8]) are responsible for this flat, board-like molecular arrangement.…”

Substituent effects on the thioamide group in thiobenzanilides: simultaneous conformational and acid-base equilibria

“…In this case, the dependence on solvent would be greater, but in our opinion this bond has a tour probability: the exact position of the benzene ring in 1 is not known but in benzanilide it is not coplanar with the CON plane. 23 Additive relationship Equation (3) presumes both the dependence on constants s and the additivity of substituent effects. Since the two presumptions are independent, 19 the additivity can be tested in a separate test.…”

Normal vibrational analysis of benzanilide. A model for poly(p-phenylene terephthalamide)

“…R4, = <(CCC) (6,7,2) RT8 = CC' opb 8 1 3 = r(N-H) (10,W R46 = <(CNH) (5,10,13) R79 = CH opb R,, = r(N-C') (10,W R4j = <(HNC') (13,10,15) (10,15,14) RE2 = CH opb R,, = r(C-H) (1722) RbO = <(OC'C) (14,15,16) RE3 = CH opb Rl0 = r(C-C) (5,6) = <(CCC) (4, 5,6) R7, = NH opb RI8 = r(C-H) (18,231 R51 = <(NC'C) (10,15,16) RE, = C-C tor R,, = r(C-H) (19,241 R52 = <(CCC') (21, 16,15) RE, = C-C tor…”