An Experimental and Theoretical Conformational Study of a Series of Substituted 3-cyclohexyl-2-phenyl-1,3-thiazolidin-4-ones


  •  Kevin Cannon    
  •  Linda Mascavage    
  •  Kurt Kistler    
  •  John Tierney    
  •  Hemant Yennawar    
  •  Anthony Lagalante    

Abstract

A series of novel 3-cyclohexyl-2-phenyl-1,3-thiazolidin-4-one derivatives with substituents on the 2-phenyl ring were synthesized, and a study of their solid state and solution conformations was effected. In solution the thiazolidin-4-one ring preferred the C2 phenyl in a pseudo-equatorial orientation and the solid state indicated a preference for the C2 phenyl being in a pseudo-axial orientation. Less robust substituent chemical shift (SCS) correlations utilizing 13C NMR were observed in this instance than in prior studies. Molecular modeling studies using Møller-Plessett second-order perturbation theory (MP2) indicate that the thiazolidinone ring and cyclohexyl ring conformations exhibit a global minimum consistent with the solution studies.


This work is licensed under a Creative Commons Attribution 4.0 License.
  • Issn(Print): 1916-9698
  • Issn(Onlne): 1916-9701
  • Started: 2009
  • Frequency: quarterly

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