Abstract
1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone (C17H12NOCl) (1) was synthesized and the crystal structure was determined. Compound 1 crystallizes in the monoclinic space group P21/n with a = 4.761(3) Å, b = 20.347(1) Å, c = 13.773(2) Å, β = 92.89(3)°, V = 1332.4(3) Å3, Z = 4, D c = 1.404 g cm−3, μ(Mo Kα) = 0.28 mm−1, and R = 0.036 for 2680 reflections [I > 2σ(I)]. Molecule 1 is not planar, and the dihedral angle between the naphthaldeyde plane A [C1–C11, 01] and the 4-chloroaniline plane B [C12–C17, C11, N1] is 20.1(3)°. An intramolecular hydrogen bond occurs between the hydroxyl oxygen and imine nitrogen atoms [2.528(3) Å]. IR, 1H NMR, and UV measurements and AM1 semiempirical quantum mechanical calculations support the keto form found in the X-ray structure.
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Ünver, H., Kabak, M., Zengin, D.M. et al. Keto–enol tautomerism, conformations, and structure of 1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone. Journal of Chemical Crystallography 31, 203–209 (2001). https://doi.org/10.1023/A:1014395132751
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DOI: https://doi.org/10.1023/A:1014395132751