A Novel Halogen Bond Acceptor: 1-(4-Pyridyl)-4-Thiopyridine (PTP) Zwitterion

Ding, Xin; Tuikka, Matti; Haukka, Matti

doi:10.3390/cryst10030165

Cited by 7 publications

(4 citation statements)

References 51 publications

(23 reference statements)

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“…Overall, the R IS values are the same on average for 1,4‐ and 1,3‐DITFB XB complexes with thioureas [5,7,41,46,48–52] . The shortest XB distances observed here are less than 0.10 Å longer than the shortest ones ( R IS =0.82) found from the literature for XB contacts between DITFB and sulfur atom [7,41,53,54] …”

Section: Resultssupporting

confidence: 69%

Thiourea‐Based Tritopic Halogen‐Bonding Acceptors

Happonen¹,

Mattila²,

Peshev³

et al. 2023

Chemistry An Asian Journal

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A series of thiourea‐based tritopic receptor molecules were synthesized to be used as building blocks for halogen‐bonded assemblies. Here, 16 new receptor molecules were synthesized from two different 2,4,6‐trialkyl‐1,3,5‐tris(bromomethyl)benzene starting materials via tris(isothiocyanatomethyl)benzene intermediates. The alkyl substituents in the benzene ring proved to be important for isothiocyanate group formation instead of competing thiocyanate group. The synthesis route allowed us to synthesize the isothiocyanate intermediates and further the receptor molecules without the typically used and highly toxic thiophosgene. The synthesized receptor molecules were used to study their halogen‐bond acceptor properties with diiodotetrafluorobenzene donors by single‐crystal X‐ray diffraction method. We were able to obtain five new crystal structures of halogen‐bonded complexes, in which all receptors showed two to four accepted C−I⋅⋅⋅S halogen bonds. The observed halogen bonds were highly directional and showed large variation in C=S⋅⋅⋅I acceptor angles, indicating flexible acceptor properties of sulfur.

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Section: Resultssupporting

confidence: 69%

Thiourea‐Based Tritopic Halogen‐Bonding Acceptors

Happonen¹,

Mattila²,

Peshev³

et al. 2023

Chemistry An Asian Journal

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“…In recent years, crystal engineering has proved to be a viable approach for fine-tuning properties of solids in various fields of research such as energetic materials, − optical and semiconductor industries, − and agrochemicals . The pharmaceutical field is no exception, which is confirmed by the exponentially increasing number of studies of pharmaceutical co-crystals both in industry and academia .…”

Section: Introductionmentioning

confidence: 99%

Two-Component Molecular Crystals: What Is the Difference between Drug–Drug, Drug–GRAS, and CF–CF Databases? Evaluation of Melting Points and Ideal Solubility of Unknown Co-crystals

Perlovich

2021

Crystal Growth & Design

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Based on literature analysis, we have built a database containing fusion temperatures and enthalpies of twocomponent molecular co-crystals and individual compounds (2170 co-crystals). The distribution functions of two-component crystals have been analyzed using their fusion temperatures, both for the database as a whole and separately for Drug−Drug, Drug− generally recognized as safe (GRAS), Drug−CF, and CF1−CF2 databases. A comparative analysis has been done of the co-crystal distribution by classes of compounds, I ("Between"), II ("Higher"), and III ("Low"), for the general database and six small databases. Correlation equations connecting the melting points of the co-crystals and individual components have been obtained, which has enabled us to design co-crystals with predictable melting temperatures. The effect of the difference between the melting temperatures of individual co-crystal components on the probability of formation of co-crystals of different groups (I−III) has been analyzed. An approach has been developed for evaluating the ideal solubility of co-crystals based on the knowledge of the ideal solubility of one of the co-crystal individual components only.

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“…Erdelyi et al investigated weak interactions with 15 N NMR studies and observed changes in the chemical shift of maximum 1.2 ppm . We are not aware of any molecular XB adduct based on a weak interaction without additional electron-withdrawing halogen substituents which has been studied both in the solid state and solution. − Herein we present our results on such a system and report the crystal structure of the adduct between the weak XB donor iodobenzene ( 2 ) and the good XB acceptor quinuclidine ( 1 ) (Figure ).…”

mentioning

confidence: 99%

Weak yet Decisive: Molecular Halogen Bond and Competing Weak Interactions of Iodobenzene and Quinuclidine

et al. 2021

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The halogen bonded adduct between the commonly used constituents quinuclidine and iodobenzene is based on a single weak nitrogen–iodine contact, and the isolation of this adduct was initially unexpected. Iodobenzene does not contain any electron-withdrawing group and therefore represents an unconventional halogen bond donor. Based on excellent diffraction data of high resolution, an electron density study was successfully accomplished and confirmed one of the longest N···I molecular halogen bonds with a distance of 2.9301(4) Å. The topological analysis identified the XB as a directional but weak σ hole interaction and revealed secondary contacts between peripheral regions of opposite charge. These additional contacts and their competition with a nitrogen-based interaction were confirmed by NOESY experiments in solution. Integration enabled us to determine the relative NOE ratios and provided insight regarding the existing interactions.

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A Novel Halogen Bond Acceptor: 1-(4-Pyridyl)-4-Thiopyridine (PTP) Zwitterion

Cited by 7 publications

References 51 publications

Thiourea‐Based Tritopic Halogen‐Bonding Acceptors

Thiourea‐Based Tritopic Halogen‐Bonding Acceptors

Two-Component Molecular Crystals: What Is the Difference between Drug–Drug, Drug–GRAS, and CF–CF Databases? Evaluation of Melting Points and Ideal Solubility of Unknown Co-crystals

Weak yet Decisive: Molecular Halogen Bond and Competing Weak Interactions of Iodobenzene and Quinuclidine

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