Jump to main content
Jump to site search

Issue 20, 2014
Previous Article Next Article

When two symmetrically independent molecules must be different: “Crystallization-induced diastereomerization” of chiral pinanyl sulfone

Author affiliations

Abstract

According to X-ray data, homochiral pinanyl sulfone crystallizes as an asymmetric dimer formed by pairwise H-bonds involving stereochemically different oxygen atoms of sulfonyl groups of molecules A and B. Thus, a pro-R atom is invoked for the construction of a relevant H-bond in molecule A, but in the case of molecule B only a pro-S atom is involved. Newly formed chiral sulfur atoms take opposite chirality in molecules A and B, while the configuration of the pinane skeleton remains unchanged. Such a stereochemical transformation is called “crystallization-induced diastereomerization”. The stability of the asymmetric dimer found in the crystal was evaluated within the framework of DFT (B3LYP, 6-31G (d,p)) and studied via IR spectroscopy in solution.

Graphical abstract: When two symmetrically independent molecules must be different: “Crystallization-induced diastereomerization” of chiral pinanyl sulfone

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Dec 2013, accepted on 16 Feb 2014 and first published on 18 Feb 2014


Article type: Paper
DOI: 10.1039/C3CE42642D
Author version
available:
Download author version (PDF)
CrystEngComm, 2014,16, 4314-4321

  •   Request permissions

    When two symmetrically independent molecules must be different: “Crystallization-induced diastereomerization” of chiral pinanyl sulfone

    O. A. Lodochnikova, V. A. Startseva, L. E. Nikitina, A. V. Bodrov, A. E. Klimovitskii, E. N. Klimovitskii and I. A. Litvinov, CrystEngComm, 2014, 16, 4314
    DOI: 10.1039/C3CE42642D

Search articles by author

Spotlight

Advertisements