The iodine–oxygen halogen bond: solid-state structures of 3-iodopropiolamides

Kratzer, Philipp; Ramming, B.; Römisch, Steven; Maas, Gerhard

doi:10.1039/c5ce00365b

Cited by 10 publications

(5 citation statements)

References 67 publications

(79 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The iodine-oxygen distance is 2.55 Å and shorter than the sum of the van der Waals radii, which are the shortest C-I•••O contacts reported so far. [11][12][13] In agreement with the very short For better understanding and visualizing the bonding feature in the complexes, the 3D deformation electron density maps were showed in Figure S8. These maps clearly show the nonspherical distribution of electron density around the halogen (X) atom.…”

Section: Computational Simulationsupporting

confidence: 76%

Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly

Zha

Dong

Miao

et al. 2016

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

Halogen bonding with high specificity and directionality in the geometry has proven to be an important type of noncovalent interaction to fabricate and control 2D molecular architectures on surfaces. Herein, we first report how the orientation of the ester substituent for thienophenanthrene derivatives (5,10-DBTD and 5,10-DITD) affects positive charge distribution of halogens by density functional theory, thus determining the formation of an intermolecular halogen bond and different self-assembled patterns by scanning tunneling microscopy. The system presented here mainly includes heterohalogen X···O═C and X···S halogen bonds, H···Br and H···O hydrogen bonds, and I···I interaction, where the directionality and strength of such weak bonds determine the molecular arrangement by varying the halogen substituent. This study provides a detailed understanding of the role of ester orientation, concentration, and solvent effects on the formation of halogen bonds and proves relevant for identification of multiple halogen bonding in supramolecular chemistry.

show abstract

Section: Computational Simulationsupporting

confidence: 76%

Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly

Zha

Dong

Miao

et al. 2016

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

show abstract

“…An analysis of the remaining 122 data sets shows that in most cases I···O interactions are not present due to the formation of halogen bonds with other halogen bond acceptors, while the oxygen atom participates in hydrogen bond formation. Several examples of such behavior are cocrystals of morpholine with β-iodophenylacetylene (refcodes MORIPA and MORIPA01); , morpholine and 1,3-diiodotetrafluorobenzene (refcode WIGQUB), where only I···N halogen bonds are formed; and the reported structure of 3-iodo-1-(morpholin-4-yl)prop-2-yn-1-one (refcode LUNLAJ), where the I···O halogen bond is formed with the ketone oxygen atom. From the 21 bromine-based data sets, only 2 correspond to systems where the donor and acceptor atoms are on different components; those are the cocrystal between morpholine and 1,4-dibromotetrafluorobenzene (refcode DIVDIW) and the 4,4-diethylmorpholinium salt of 2,5-dibromo-7,7,8,8-tetracyanoquinodimethane (refcode BOTGOG) .…”

mentioning

confidence: 99%

The Morpholinyl Oxygen Atom as an Acceptor Site for Halogen-Bonded Cocrystallization of Organic and Metal–Organic Units

Nemec

Piteša

Friščić

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

We explore the halogen bond acceptor potential of the morpholinyl oxygen atom in the synthesis of cocrystals involving organic and metal−organic units, by using N-aminomorpholine either as a potential halogen bond acceptor or as a reagent to insert a morpholine moiety into larger organic and copper(II)-based metal−organic building blocks. Challenged against four well-known halogen bond donor molecules differing in binding geometry and composition, these three morpholinecontaining units have yielded a total of seven previously not reported cocrystals, of which six (86%) exhibited the formation of I•••O or Br•••O halogen bonds to the morpholinyl oxygen atom. The results illustrate the possibility to systematically insert and use a morpholine group as an efficient halogen bond acceptor into organic and metal−organic structures, thus enabling cocrystal formation.

show abstract

“…Although the arrangement of diynes in the present article stands no chance of undergoing topochemical polymerization, we suggest that in other systems prone to polymerization, replacing Br, I or H atoms by Cl atoms in their diyne groups might result in successful PolyChloroDiAcetylene (PCDA) formation as well. This work also contributes to an emerging research theme, namely the concept of orthogonal molecular interactions such as HBs and XBs (Kratzer et al, 2015;Takemura et al, 2014;Voth et al, 2009), which may find applications in medicinal chemistry and chemical biology (Wilcken et al, 2013).…”

Section: Chemical Contextmentioning

confidence: 95%

Isomorphous crystal structures of chlorodiacetylene and iododiacetylene derivatives: simultaneous hydrogen and halogen bonds on carbonyl

et al. 2017

View full text Add to dashboard Cite

The crystal structures of tert-butyl (5-chloropenta-2,4-diyn-1-yl)carbamate, C 10 H 12 ClNO 2 (II), and tert-butyl (5-iodopenta-2,4-diyn-1-yl)carbamate, C 10 H 12 INO 2 (IV), are isomorphous to previously reported structures and accordingly their molecular and supramolecular structures are similar. In the crystals of (II) and (IV), molecules are linked into very similar two-dimensional wall organizations with antiparallel carbamate groups involved in a combination of hydrogen and halogen bonds (bifurcated N-HÁ Á ÁO C and C C-XÁ Á ÁO C interactions on the same carbonyl group). There is no long-range parallel stacking of diynes, so the topochemical polymerization of diacetylene is prevented. A Cambridge Structural Database search revealed that C C-XÁ Á ÁO C contacts shorter than the sum of the van der Waals radii are scarce (only one structure for the C C-ClÁ Á ÁO C interaction and 13 structures for the similar C C-IÁ Á ÁO C interaction).

show abstract

The iodine–oxygen halogen bond: solid-state structures of 3-iodopropiolamides

Cited by 10 publications

References 67 publications

Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly

Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly

The Morpholinyl Oxygen Atom as an Acceptor Site for Halogen-Bonded Cocrystallization of Organic and Metal–Organic Units

Isomorphous crystal structures of chlorodiacetylene and iododiacetylene derivatives: simultaneous hydrogen and halogen bonds on carbonyl

Contact Info

Product

Resources

About