Next Article in Journal
Volumetric Scalability of Microfluidic and Semi-Batch Silk Nanoprecipitation Methods
Next Article in Special Issue
Secondary Metabolism Rearrangements in Linum usitatissimum L. after Biostimulation of Roots with COS Oligosaccharides from Fungal Cell Wall
Previous Article in Journal
Molecular Dynamics and MM-PBSA Analysis of the SARS-CoV-2 Gamma Variant in Complex with the hACE-2 Receptor
Previous Article in Special Issue
NMR, LC-MS Characterization of Rydingia michauxii Extracts, Identification of Natural Products Acting as Modulators of LDLR and PCSK9
 
 
Article

Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives

1
Department of Applied Chemistry (Japanese Association of Bio-Intelligence for Well-Being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan
2
Graduate School of Engineering and Science, Shibaura Institute of Technology, 307 Fukasaku, Minuma-ku, Saitama 337-8570, Japan
3
Center for Medical and Nursing Education, Division of Basic Sciences, Tokyo Women’s Medical University, 8-1 Kawada-cho, Shinjuku-ku, Tokyo 162-8666, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: Roman Dembinski, Diego Muñoz-Torrero and Giuseppe Cirillo
Molecules 2022, 27(7), 2369; https://doi.org/10.3390/molecules27072369
Received: 3 March 2022 / Revised: 2 April 2022 / Accepted: 4 April 2022 / Published: 6 April 2022
(This article belongs to the Special Issue Molecules in 2022)
The halogen bond has been widely used as an important supramolecular tool in various research areas. However, there are relatively few studies on halogen bonding related to molecular chirality. 3-(2-Halophenyl)quinazoline-4-thione derivatives have stable atropisomeric structures due to the rotational restriction around an N-C single bond. In X-ray single crystal structures of the racemic and optically pure N-C axially chiral quinazoline-4-thiones, we found that different types of intermolecular halogen bonds (C=S⋯X) are formed. That is, in the racemic crystals, the intermolecular halogen bond between the ortho-halogen atom and sulfur atom was found to be oriented in a periplanar conformation toward the thiocarbonyl plane, leading to a syndiotactic zig-zag array. On the other hand, the halogen bond in the enantiomerically pure crystals was oriented orthogonally toward the thiocarbonyl plane, resulting in the formation of a homochiral dimer. These results indicate that the corresponding racemic and optically pure forms in chiral molecules are expected to display different halogen bonding properties, respectively, and should be separately studied as different chemical entities. View Full-Text
Keywords: halogen bonds; axial chirality; atropisomers; quinazolinones; thiones halogen bonds; axial chirality; atropisomers; quinazolinones; thiones
Show Figures

Figure 1

MDPI and ACS Style

Matsui, R.; Niijima, E.; Imai, T.; Kobayashi, H.; Hori, A.; Sato, A.; Nakamura, Y.; Kitagawa, O. Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives. Molecules 2022, 27, 2369. https://doi.org/10.3390/molecules27072369

AMA Style

Matsui R, Niijima E, Imai T, Kobayashi H, Hori A, Sato A, Nakamura Y, Kitagawa O. Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives. Molecules. 2022; 27(7):2369. https://doi.org/10.3390/molecules27072369

Chicago/Turabian Style

Matsui, Ryosuke, Erina Niijima, Tomomi Imai, Hiroyuki Kobayashi, Akiko Hori, Azusa Sato, Yuko Nakamura, and Osamu Kitagawa. 2022. "Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives" Molecules 27, no. 7: 2369. https://doi.org/10.3390/molecules27072369

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop