Conformational study and structure of N-(2,5-methylphenyl)salicylaldimine
JOURNAL OF MOLECULAR STRUCTURE, cilt.443, sa.1-3, ss.123-130, 1998 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 443 Sayı: 1-3
- Basım Tarihi: 1998
- Doi Numarası: 10.1016/s0022-2860(97)00382-7
- Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.123-130
- Anahtar Kelimeler: X-ray, Schiff base, AM1, photochromism, thermochromism, PHOTOCHROMISM, THERMOCHROMISM, GLASSES
- Ankara Üniversitesi Adresli: Evet
Özet
N-(2,5-methylphenyl)salicylaldimine (C15H15NO) has been investigated by X-ray analysis and AMI semi-empirical quantum mechanical method. The crystal is in the orthorhombic space group P2(1)2(1)2(1) with a = 6.839(1), b = 7.720(4), c = 23.183(3) Angstrom, V = 1224.1(2) Angstrom(3), Z = 4, D-c = 1.222 g cm(-1) and mu(MO K alpha) = 0.076 mm(-1). The title structure was solved by direct methods and refined to R = 0.0364 for 1489 reflections [I > 2 sigma(I)] by full-matrix anisotropic least-squares methods. The title compound is photochromic and the molecule is not planar. There is a strong intramolecular hydrogen bond of distance 2.604(2) Angstrom between the hydroxyl oxygen atom and imine nitrogen atom, the hydrogen atom essentially being bonded to the oxygen atom. Minimum energy conformations from AMI were calculated as a function of three torsion angles, theta(1) (C8-N1-C7-C6), theta(2) (C9-C8-N1-C7) and theta(3) (N1-C7-C6-C5), varied every 10 degrees. The optimized geometry of the crystal structure corresponding to non-planar conformation is the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded hydrogen-hydrogen repulsions. (C) 1998 Elsevier Science B.V.