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

J.T. Schirlin, D.A. Wann, S.F. Bone, H.E. Robertson, D.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. © 2009 Elsevier B.V. All rights reserved.
Original languageEnglish
Pages (from-to)103-108
JournalJOURNAL OF MOLECULAR STRUCTURE
Volume922
Issue number1-3
DOIs
Publication statusPublished - 30 Mar 2009

Bibliographical note

Cited By (since 1996):1

Export Date: 1 October 2013

Source: Scopus

CODEN: JMOSB

doi: 10.1016/j.molstruc.2009.01.032

Language of Original Document: English

Correspondence Address: Rankin, D.W.H.; School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom; email: d.w.h.rankin@ed.ac.uk

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Keywords

  • Ab initio calculations
  • Additivity
  • Gas electron diffraction
  • Ring distortion
  • Unsaturated five-membered heterocycles
  • Benzene
  • Chlorine
  • Electron diffraction

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