Abstract
This study expands and combines concepts from two of our earlier studies. One study reported the complementary halogen bonding and π-π charge transfer complexation observed between isomeric electron rich 4-N,N-dimethylaminophenylethynylpyridines and the electron poor halogen bond donor, 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene while the second study elaborated the ditopic halogen bonding of activated pyrimidines. Leveraging our understanding on the combination of these non-covalent interactions, we describe cocrystallization featuring ditopic halogen bonding and π-stacking. Specifically, red cocrystals are formed between the ditopic electron poor halogen bond donor 1-(3,5-dinitrophenylethynyl)-2,4,6-triflouro-3,5-diiodobenzene and each of electron rich pyrimidines 2- and 5-(4-N,N-dimethyl-aminophenylethynyl)pyrimidine. The X-ray single crystal structures of these cocrystals are described in terms of halogen bonding and electron donor-acceptor π-complexation. Computations confirm that the donor-acceptor π-stacking interactions are consistently stronger than the halogen bonding interactions and that there is cooperativity between π-stacking and halogen bonding in the crystals.
Highlights
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations
Earlier we described cocrystallization based on cooperative halogen bonding and electron donorelectron acceptor π-complexation to form colored cocrystals [12]
The cooperativity and competition between the different intermolecular interactions was explored by carrying out single point energy calculations on the relevant clusters from the crystal structure using the Gaussian16
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Halogen bonding and π-stacking have been incorporated as key cooperative non-covalent interactions in the [2+2] photoreaction in oocrystals including dipyridylethylenes [8]. Earlier we described cocrystallization based on cooperative halogen bonding and electron donorelectron acceptor π-complexation to form colored cocrystals [12]. -ABABπ-stacked, halogen bonded, bonded, In athe separate study demonstrated that electron rich pyrimidines, bonded, molecules. In a separate study we demonstrated that electron rich pyrimidines, molecules. In a separate study demonstrated that electron rich pyrimidines, related related to molecule. 1 particular and 2 aswe both ditopic that halogen bond acceptors and electron rich aromatics pyrimidines.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
