Linear free energy relationships of C-13 NMR chemical shifts in 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-ones(thiones)


Agirbas H., Kemal B.

JOURNAL OF MOLECULAR STRUCTURE, vol.1053, pp.61-65, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1053
  • Publication Date: 2013
  • Doi Number: 10.1016/j.molstruc.2013.09.011
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Page Numbers: pp.61-65

Abstract

Linear free energy relationships (LFER) were applied to the C-13 NMR chemical shifts in 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-ones(thiones). The correlation analysis for the substituent-induced chemical shifts (SCS) with inductive and resonance parameters (sigma, F and R) were carried out by using SSP (single substituent parameter) and DSP (dual substituent parameter). The presented calculation accounts satisfactorily for the polar and resonance substituent effects operating at benzoxazepine carbon atoms. Negative rho values were found for several correlations (reverse substituent effect). For a better understanding of the results, density functional theory (DFT) calculations were performed to determine the preferred geometry and to calculate the theoretical C-13 NMR chemical shifts. (C) 2013 Elsevier B.V. All rights reserved.