Additivity of ring geometry distortion effects in unsaturated five-membered heterocyclic rings

Julien T. Schirlin, Derek A. Wann, Simon F. Bone, Heather E. Robertson, David W. H. Rankin

Research output: Contribution to journalArticlepeer-review

Abstract

Empirical rules for the prediction of structures are valuable, providing aids to understanding and prediction that complement sophisticated computational methods. In this work, the structures of unsaturated five-membered rings have been predicted using sets of parameters describing distortions caused by substitutions in benzene and other rings. Effects on the structures of unsaturated five-membered rings due to both ring-member and substituent changes are found to be additive. Moreover, distortions caused by chlorine substitution observed for aromatic six-membered rings can be directly transferred to unsaturated five-membered rings with satisfying accuracy. The analysis has made use of data obtained by study of the structures of 2,5-dichlorothiophene and 3,4-dichloro-1,2,5-thiadiazole by gas-phase electron diffraction and computational chemistry methods.

Original languageEnglish
Pages (from-to)103-108
Number of pages6
JournalJournal of Molecular Structure
Volume922
Issue number1-3
DOIs
Publication statusPublished - 2009

Keywords

  • Gas electron diffraction
  • Ab initio calculations
  • Ring distortion
  • Unsaturated five-membered heterocycles
  • Additivity
  • MOLECULAR-ORBITAL METHODS
  • VALENCE BASIS-SETS
  • SHELL PHOTOELECTRON-SPECTRA
  • ELECTRON-DIFFRACTION
  • PERTURBATION-THEORY
  • CRYSTALLINE PHASES
  • 2ND-ROW ELEMENTS
  • GAS-PHASE
  • THIOPHENE
  • 1,2,5-THIADIAZOLE

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