Scheme 1: General Mechanism of the Formation of Schiff Base.

Table 3

IR data of the compounds, A1 and A2.

Absorption band, υ/cm⁻¹

Compound
υ(NH) + υ(OH) υ(Cѕр₃-H) υ(C=N) υ(C=C)aromatic

A1 3350 m, 3308 s 2974-2842 w 1605 m 1540-1480 s

A2 3542 s, 3405 m, 3129 s 2967 s 1610 m 1543-1471 s

Abbreviations: s=strong; m=medium; w=weak.

Table 4

¹H NMR chemical shifts, δ/ppm, and coupling constants J/Hz of Schiff

bases, A1 and A2.

Chemical shifts, δ/ppm*

Proton
Coupling constant, J/Hz

A1 A2

H-2 8.41 (s) 8.37 (s)

8.46 (t) 8.42 (t)

H-1a
J=6.0 J=6.0

H-1b 3.59 (m) 3.58 (m)

1.15(t) 1.14 (t)

H-1c
J=7.0 J=7.0

H-3’a 3.82 (s) -

6.97 (dd) 6.81 (dd)

H-4’
J=1.5, 8.0 J=1.5, 8.0

6.79 (t)
6.66 (t)
H-5’ J=8.0
J=7.5

7.56 (dd) 7.37 (d)

H-6’
J=1.0, 8.0 J=7.5

H-1” 11.40 (s) 11.35 (s)

O-H 9.20 (s) 10.21 (s)

* In brackets: multiplicity of signals denoted as: (s) = singlet; (d) = doublet;

(dd) = double of doublets; (t) = triplet.
Table 5

¹³C NMR chemical shifts, δ/ppm of Schiff bases, A1 and A2.

¹³C, δ/ppm
Carbon
A1 A2

C-1 176.4 176.4

C-2 138.9 139.7

C-1b 38.2 38.2

C-1c 14.6 14.6

C-1’ 120.8 120.9

C-2’ 147.9 145.1

C-3’ 145.9 145.5

C-3’a 55.8 -

C-4’ 112.7 116.3

C-5’ 118.9 119.0

C-6’ 118.0 117.0