The reaction of triphenylarsine oxide with ethyl iodo‐acetate leading to triphenyl (carboethoxy)methylarsonium triiodide

Abalonin, B. E.; Низамов, И. С.; Krivolapov, Dmitry B.; Nizamov, I. S.; Khaibullin, R. N.; Al’metkina, L. A.; Батыева, Э. С.; Литвинов, И. А.

doi:10.1002/hc.20050

Cited by 3 publications

(3 citation statements)

References 10 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…( c , d ) Histograms showing the distribution of 64 As···N contacts and ∠R–As···N in 43 crystals emerged from a CSD search, with the normal distribution curve in red. Illustration of inter- and intramolecular arsenic bonds in some crystals catalogued in the CSD, including: ( e ) 8,8′-(phenylarsanediyl)diquinoline [ 193 ]; ( f ) 1-phenyl-2-(triphenyl-arsanylidene)ethan-1-one [ 194 ]; ( g ) triphenyl(ethoxycarbonylmethyl)arsonium tri-iodide [ 196 ]; ( h ) 2,3-bis(diphenylarsino)pyrazine [ 195 ]; ( i ) tetraphenylarsonium trifluoroacetylide-dicyanomethanide [ 197 ]; ( j ) diazido-chloro-pyridyl-arsenic(III) [ 198 ]. Selected bond lengths and angles are shown in Å and degree, respectively.…”

Section: Arsenic In Crystalsmentioning

confidence: 99%

“…Three other crystal systems in which intermolecular arsenic bonds are evident are shown in Figure 13 g,i,j. The longest of these is in the crystal of the triodide salt, DAQMEO [ 196 ], with r (As···I) = 4.640 Å. Although it is significantly longer than the sum of the vdW radii of As and I (3.92 Å), it is directional, with ∠C–As···I = 167.4°.…”

Section: Arsenic In Crystalsmentioning

confidence: 99%

“…A very similar feature occurs in the two crystals shown in Figure 13 i (DENBON) [ 197 ] and Figure 13 j (HUGLIE) [ 198 ]; the As···N intermolecular distances are longer than the sum of the vdW radii of As and N, 3.54 Å ( r vdW (As) = 1.88 Å and r vdW (N) = 1.66 Å). In the case of DAQMEO [ 196 ] ( Figure 13 g) and DENBON [ 197 ] ( Figure 13 i), the Lewis bases forming the As···I and As···N arsenic bonds are also involved in H···I and H···N hydrogen bonds with the arene moiety (not shown) and these are probably the primary interactions that cause the formation of secondary pnictogen bonds.…”

Section: Arsenic In Crystalsmentioning

confidence: 99%

See 2 more Smart Citations

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

Varadwaj

Marques

et al. 2022

Molecules

View full text Add to dashboard Cite

In chemical systems, the arsenic-centered pnictogen bond, or simply the arsenic bond, occurs when there is evidence of a net attractive interaction between the electrophilic region associated with a covalently or coordinately bound arsenic atom in a molecular entity and a nucleophile in another or the same molecular entity. It is the third member of the family of pnictogen bonds formed by the third atom of the pnictogen family, Group 15 of the periodic table, and is an inter- or intramolecular noncovalent interaction. In this overview, we present several illustrative crystal structures deposited into the Cambridge Structure Database (CSD) and the Inorganic Chemistry Structural Database (ICSD) during the last and current centuries to demonstrate that the arsenic atom in molecular entities has a significant ability to act as an electrophilic agent to make an attractive engagement with nucleophiles when in close vicinity, thereby forming σ-hole or π-hole interactions, and hence driving (in part, at least) the overall stability of the system’s crystalline phase. This overview does not include results from theoretical simulations reported by others as none of them address the signatory details of As-centered pnictogen bonds. Rather, we aimed at highlighting the interaction modes of arsenic-centered σ- and π-holes in the rationale design of crystal lattices to demonstrate that such interactions are abundant in crystalline materials, but care has to be taken to identify them as is usually done with the much more widely known noncovalent interactions in chemical systems, halogen bonding and hydrogen bonding. We also demonstrate that As-centered pnictogen bonds are usually accompanied by other primary and secondary interactions, which reinforce their occurrence and strength in most of the crystal structures illustrated. A statistical analysis of structures deposited into the CSD was performed for each interaction type As···D (D = N, O, S, Se, Te, F, Cl, Br, I, arene’s π system), thus providing insight into the typical nature of As···D interaction distances and ∠R–As···D bond angles of these interactions in crystals, where R is the remainder of the molecular entity.

show abstract

Section: Arsenic In Crystalsmentioning

confidence: 99%

Section: Arsenic In Crystalsmentioning

confidence: 99%

Section: Arsenic In Crystalsmentioning

confidence: 99%

See 1 more Smart Citation

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

Varadwaj

Marques

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

The Reaction of Triphenylarsine Oxide with Ethyl Iodo‐acetate Leading to Triphenyl (Carboethoxy)methylarsonium Triiodide.

Abalonin¹,

Низамов

Krivolapov

et al. 2005

ChemInform

View full text Add to dashboard Cite

Organo-arsenic compounds S 0110The Reaction of Triphenylarsine Oxide with Ethyl Iodo-acetate Leading to Triphenyl (Carboethoxy)methylarsonium Triiodide. -The structure of (III), obtained via title reaction, is established by X-ray single cristal diffraction. The reaction mechanism is discussed. -(ABALONIN, B. E.; NIZAMOV*, I. S.; KRIVOLAPOV, D. B.; NIZAMOV, I. D.; KHAIBULLIN, R. N.; AL'METKINA, L. A.; BATYEVA, E. S.; LITVINOV, I. A.; Heteroat. Chem. 15 (2004) 7, 482-485; Kazan State Pedagog. Univ., Kazan' 420021, Russia; Eng.) -H. Haber 13-191

show abstract

Crystal structure of 2-(4-methylphenyl)-2-oxo-1-(phenyliodonio)-1-(triphenylarsonio)ethanid tetrafluoroborate solved from X-ray powder data

Миронов¹,

Чернышев²,

Matveeva³

et al. 2013

Zeitschrift Für Kristallographie - Crystalline Materials

View full text Add to dashboard Cite

The crystal structure of 2-(4-methylphenyl)-2-oxo-1-(phenyliodonio)-1-(triphenylarsonio)ethanid tetrafluoroborate, C33H27AsIO+BF4 –, was solved and refined from laboratory X-ray powder diffraction data in combination with a DFT calculation (CoK α1, a=24.427(2) Å, b = 13.3412(18) Å, c=22.399(2) Å, β = 119.49(2)°, S.G. C2/c, R p/R wp = 0.030/0.039). The main features of the C33H27AsIO+BF4 – structure are similar to those reported previously for arsenium and phosphorous organic compounds. The distinctive features are short I … O and I … F (2.743(19) and 2.916(17) Å, respectively) intermolecular contacts, also observed previously in the same type of compound, refined from single crystal data.

show abstract

The reaction of triphenylarsine oxide with ethyl iodo‐acetate leading to triphenyl (carboethoxy)methylarsonium triiodide

Cited by 3 publications

References 10 publications

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

The Reaction of Triphenylarsine Oxide with Ethyl Iodo‐acetate Leading to Triphenyl (Carboethoxy)methylarsonium Triiodide.

Crystal structure of 2-(4-methylphenyl)-2-oxo-1-(phenyliodonio)-1-(triphenylarsonio)ethanid tetrafluoroborate solved from X-ray powder data

Contact Info

Product

Resources

About