Experimental and theoretical investigation of 1J(CC) and (n)J(CC) coupling constants in strychnine

Org Lett. 2012 Oct 5;14(19):5098-101. doi: 10.1021/ol302366s. Epub 2012 Sep 20.

Abstract

A relatively unexplored and unexploited means of establishing molecular structure, stereochemistry, and probing vicinal bond angles is through the use of long-range (13)C-(13)C coupling constants. The measurement of these multifunctional, diagnostic (3)J(CC) couplings has not been reported on sample amounts viable for the practicing organic chemist. A generalized protocol for the measurement of (1)J(CC) and (3)J(CC) couplings using a 4.6 mg sample of strychnine as a model compound is described, and the utility of DFT calculations for the prediction of these useful molecular descriptors and the congruence of the calculated and experimental data is demonstrated.

MeSH terms

  • Molecular Structure
  • Stereoisomerism
  • Strychnine / chemistry*

Substances

  • Strychnine