A chiral photochromic Schiff base: (R)-4-methoxy-2-[(1-phenylethyl)iminomethyl]phenol

Abstract

The title chiral photochromic Schiff base compound, C16H17NO2, was synthesized from (R)-1-phenyl­ethyl­amine and 5-methoxy­salicylaldehyde. The mol­ecule of the title compound exists in the phenol–imine tautomeric form. The dihedral angle between the two aromatic rings is 62.61 (11)°. An intra­molecular O—H⋯N hydrogen bond with an O⋯N distance of 2.589 (2) Å is observed. The crystal packing is stabilized by C—H⋯π inter­actions involving the aromatic ring.

Synthesis, characterization, crystal structure and theoretical studies of new chiral Schiff base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne

“…Selected bond distances and angles are listed in Table 3, in comparison with the calculated values at the B3LYP level. All bond distances and angles are normal and are in good agreement with those reported in similar Schiff-base compounds [26][27][28][29]. The C7=N1 and C8-N1 bond lengths of 1.277(2) Å and 1.4775(19) Å , respectively, conform to the value for double and single bonds, as in similar Schiffbase compounds [26][27][28][29].…”

“…All bond distances and angles are normal and are in good agreement with those reported in similar Schiff-base compounds [26][27][28][29]. The C7=N1 and C8-N1 bond lengths of 1.277(2) Å and 1.4775(19) Å , respectively, conform to the value for double and single bonds, as in similar Schiffbase compounds [26][27][28][29]. The C1-C7-N1 and C7-N1-C8 bond angles are 124.89(15)8 and 117.67(14)8, respectively, which is consistent with the sp 2 hybrid character of the C7 and N1 atoms [26][27][28][29].…”

“…The C7=N1 and C8-N1 bond lengths of 1.277(2) Å and 1.4775(19) Å , respectively, conform to the value for double and single bonds, as in similar Schiffbase compounds [26][27][28][29]. The C1-C7-N1 and C7-N1-C8 bond angles are 124.89(15)8 and 117.67(14)8, respectively, which is consistent with the sp 2 hybrid character of the C7 and N1 atoms [26][27][28][29]. The geometrical details of the hydrogen bonds of the title compound are summarized in Table 4.…”