(E)-1-[4-(2-hydroxy-5-methoxybenzylideneamino)phenyl]ethanone and (E)-1-[4-(2-hydroxy-4-methoxybenzylideneamino)phenyl]ethanone: X-ray and DFT-calculated structures

Sahin O., Buyukgungor O., Albayrak C., ODABAŞOĞLU M.

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, vol.30, no.1, pp.111-119, 2011 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 1
  • Publication Date: 2011
  • Journal Name: CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.111-119
  • Keywords: crystal structure, Schiff base, DFT, molecular electrostatic potential, CONTROLLED PROTON TAUTOMERIZATION, SCHIFF-BASES, COMPLEXES, SALICYLIDENEANILINES, THERMOCHROMISM, PHOTOCHROMISM, CONFORMATION, DENSITY, STATE
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The isomeric structures of (E)-1-[4-(2-hydroxy-5-methoxybenzylideneamino)phenyl] ethanone (I) and (E)-1-[4-(2-hydroxy-4-methoxybenzylideneamino)phenyl]ethanone (II), both C(16)H(15)NO(3), have been determined using X-ray diffraction techniques and characterized by IR, and their molecular structures have also been optimized at the B3LYP/6-31G(d,p) level using density functional theory (DFT). The energetic behaviors of the title compounds in solvent media have been examined using B3LYP method with the 6-31G(d,p) basis set by applying the polarizable continuum model (PCM). The total energies of the title compounds decrease with the increasing polarity of the solvent. In addition, DFT calculations of the title compounds' molecular electrostatic potentials (MEP) were performed at the B3LYP/6-31G(d,p) level of theory. X-ray study shows that the title compounds both have strong intramolecular O-H center dot center dot center dot N hydrogen bonds. The molecules of! are linked into a one-dimensional framework structure by C-H center dot center dot center dot pi interactions, while in II, intermolecular pi center dot center dot center dot pi interactions result in the formation of infinite chains running along the [010].