Issue 31, 2014

Tröger's base quasiracemates and crystal packing tendencies

Abstract

A family of 7 Tröger's base (TB) compounds that vary in configuration (quasiracemates, racemates, and enantiomers) and chemical substitutions (Me, Cl, and Br) has been investigated. The deliberate use of isosteric components provided a logical entry point to explore the quasiracemic behavior of TB compounds. Crystal structures of these quasiracemates contain several sets of molecular dimers organized by the complementary topologies of the quasienantiomeric components. These motifs closely mimic the local inversion symmetry environment observed with the racemic and solid-solution phases included with this study. Comparing this set of crystal structures to 105 TB entries found in the Cambridge Structural Database revealed four distinct dimeric packing patterns retrieved using TB⋯TB distance and orientation search criteria. Each motif takes advantage of the complementary topologies of the V-shaped building blocks and further highlights the importance of molecular shape to the recognition profile of these supramolecular assemblies. This approach exposed 58% of the entries (65 structures) exhibiting one or more of the pairwise relationships. Furthermore, sorting the entries based on centrosymmetric and noncentrosymmetric space groups provided evidence for a correlation between motif and crystallographic symmetry.

Graphical abstract: Tröger's base quasiracemates and crystal packing tendencies

Supplementary files

Article information

Article type
Paper
Submitted
14 Feb 2014
Accepted
24 Mar 2014
First published
24 Mar 2014

CrystEngComm, 2014,16, 7251-7258

Author version available

Tröger's base quasiracemates and crystal packing tendencies

J. T. Cross, N. A. Rossi, M. Serafin and K. A. Wheeler, CrystEngComm, 2014, 16, 7251 DOI: 10.1039/C4CE00323C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements