Papers

Peer-reviewed
2019

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

Cryst. Growth Des.
  • Shoko Kikkawa
  • ,
  • Hyuma Masu
  • ,
  • Kosuke Katagiri
  • ,
  • Misaki Okayasu
  • ,
  • Kentaro Yamaguchi
  • ,
  • Hiroshi Danjo
  • ,
  • Masatoshi Kawahata
  • ,
  • Masahide Tominaga
  • ,
  • Yoshihisa Sei
  • ,
  • Hidemasa Hikawa
  • ,
  • Isao Azumaya

Volume
19
Number
5
First page
2936
Last page
2946
Language
Publishing type
Research paper (scientific journal)
DOI
10.1021/acs.cgd.9b00159

Copyright © 2019 American Chemical Society. N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

Link information
DOI
https://doi.org/10.1021/acs.cgd.9b00159
Scopus
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85065151470&origin=inward
Scopus Citedby
https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85065151470&origin=inward
ID information
  • DOI : 10.1021/acs.cgd.9b00159
  • ISSN : 1528-7483
  • eISSN : 1528-7505
  • SCOPUS ID : 85065151470

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