Intramolecular hydrogen bonding and tautomerism in 1-[N-(4-bromophenyl)]aminomethylidene-2(1H) naphthalenone

Unver H., Zengin D., Guven K.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, cilt.30, sa.5, ss.359-364, 2000 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 30 Sayı: 5
  • Basım Tarihi: 2000
  • Doi Numarası: 10.1023/a:1009521510428
  • Dergi Adı: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.359-364
  • Anahtar Kelimeler: bidentate Schiff base ligand, intramolecular hydrogen bond, photochromism, thermochromism, tautomerism, SCHIFF-BASES, METAL-IONS, COMPLEXES
  • Ankara Üniversitesi Adresli: Hayır

Özet

1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone (C17H12NOBr) (1) was synthesized and its crystal structure was determined. Compound (1) is monoclinic, space group P2(1)/n with a = 4.808(1) Angstrom, b = 20.617(1) Angstrom, c = 13.750(1) Angstrom, beta = 93.004(1)degrees, = 1361.11(3) Angstrom (3), Z = 4, D-c = 1.592 g.cm(-3), mu (Mo K-alpha) = 3.014 mm(-1), R = 0.051 for 1013 reflections [I > 2 sigma (I)]. There is a strong intramolecular hydrogen bond of distance 2.544(2) Angstrom between the hydroxyl oxygen atom and imine nitrogen atom, the hydrogen atom essentially being bonded to the nitrogen atom, The title molecule is not planar. X-ray crystal structure determination reveals the existence of the keto (or predominantly keto) tautomer in (1). Spectra of compound (1) were observed by IR and NMR, and UV-visible spectra of (1) were studied in different solvents and acidic media.