Crystal structure and tautomerism of 1-[N-(4-iodophenyl)]aminomethylidene-2(1H)naphthalenone

Unver H., Kabak M., Zengin D., Durlu T.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, cilt.56, sa.10, ss.1003-1008, 2001 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 56 Sayı: 10
  • Basım Tarihi: 2001
  • Dergi Adı: ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1003-1008
  • Anahtar Kelimeler: photochromism, thermochromism, keto-enol tautomerism, SCHIFF-BASES, SOLID-STATE, TOPOCHEMISTRY, SPECTRA, ANILS
  • Ankara Üniversitesi Adresli: Hayır

Özet

1-[N-(4-Iodophenyl)]aminomethylidene-2(1H)naphthalenone (1) (C17H12NOI) has been studied by X-ray analysis, IR, H-1 NMR, UV and AM1 semi-empirical quantum mechanical methods. It crystallises in the monoclinic space group P2(1)/n with a=4.844(3), b=21.428(2), C=13.726(2) Angstrom, beta =93.07(2)degrees (R1=0.032 for 4132 reflections [I>2 sigma (I)]). The title compound is not planar and an intramolecular hydrogen bond connects O1 and N1 [2.530(4) Angstrom]. Complementary IR, H-1 NMR and UV measurements in the solution and solid states were carried out. Tautomerism and conformations of the title compound were also investigated by AM1 semi-empirical quantum mechanical calculations and the results are compared with the X-ray data.