Non-empirical calculations of NMR indirect spin-spin coupling constants. Part 13: configurational assignment of aminosulfonylamidines

Magn Reson Chem. 2005 Nov;43(11):937-42. doi: 10.1002/mrc.1645.

Abstract

Carbon-carbon coupling constants have been experimentally measured using the INADEQUATE pulse sequence in the series of N-[1,2-bis(dialkylamino)-2-arylethylidene]arylsulfonamides obtained from N-(1-aryl-2,2,2-trichloroethyl)amides of arylsulfonic acids. Comparison of the experimental J(C,C) in this series with those calculated at the SOPPA (Second-Order Polarization Propagator Approach) level in the model aminosulfonylamidine provided an unambiguous assignment at the C=N bond of the eight-title aminosulfonylamidines to E-configuration, while the unknown J(C,C) couplings in their inaccessible diverse Z isomers have been predicted with high reliability. The established marked difference between J(C,C) of the corresponding carbon-carbon bonds in cis and trans orientations to the nitrogen lone pair in aminosulfonylamidines provides a powerful tool in the configurational assignment at the C=N bond in a wide series of the related systems containing the C=N-SO2R moiety.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemistry*
  • Carbon Isotopes
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy / methods*
  • Magnetic Resonance Spectroscopy / standards
  • Models, Molecular
  • Molecular Structure
  • Reference Standards
  • Stereoisomerism

Substances

  • Amidines
  • Carbon Isotopes