The influence of halogen type on structural features of compounds containing α-halo-α,α-dinitroethyl moieties

Дмитриенко, Артем О.; Карноухова, Валентина А.; Potemkin, Aleksandr A.; Стручкова, Марина И.; Kryazhevskikh, Irina A.; Suponitsky, Kyrill Yu.

doi:10.1007/s10593-017-2088-7

Cited by 34 publications

(11 citation statements)

References 14 publications

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“…As mentioned in the Introduction, no Br• • • Br halogen bond was observed in the crystal structure of 1,12-dibromo-ortho-carborane 1,12-Br 2 -1,2-C 2 B 10 H 10 [28]. It should be noted that similarities and differences between bonding preferences of the bromine atom in comparison to iodine atom, on the one hand, and chlorine atom, on the other hand, was the subject of extensive studies [58][59][60][61]. Based on comparison of the crystal packing of 1-Ph-2-X-ortho-carboranes (X = F, Cl, Br, I), it was shown that both Br and I form Hal• • • π interactions, while neither Cl or F participate in such interactions [58].…”

Section: Resultsmentioning

confidence: 99%

“…Based on comparison of the crystal packing of 1-Ph-2-X-ortho-carboranes (X = F, Cl, Br, I), it was shown that both Br and I form Hal• • • π interactions, while neither Cl or F participate in such interactions [58]. Study of N-(2-halo-2,2-dinitroethyl)pyrrolidine-2,5-diones (Hal = F, Cl, Br) [59] has revealed that both Cl and Br participate in halogen bonding, but bromine interacts with the carbonyl oxygen atom (the strongest donor site), while chlorine prefers to connect to much weaker donors, namely, oxygen atoms of the nitro group. Based on the above, it becomes unclear a priori which packing motif should be expected in the crystal of 1,12-diiodo-ortho-carborane.…”

Section: Resultsmentioning

confidence: 99%

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1,12-Diiodo-Ortho-Carborane: A Classic Textbook Example of the Dihalogen Bond

et al. 2021

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The crystal structure of 1,12-diiodo-ortho-carborane 1,12-I2-1,2-C2B10H10 was determined by single crystal X-ray diffraction. In contrary to earlier studied 1,12-dibromo analogue 1,12-Br2-1,2- C2B10H10, its crystal packing is governed by the presence of the intermolecular I···I dihalogen bonds between the iodine atom attached to the carbon atom (acceptor) and the iodine atom attached to the antipodal boron atom (donor) of the carborane cage. The observed dihalogen bonds belong to the II type and are characterized by classical parameters: shortened I⋯I distance of 3.5687(9) Å, C–I⋯I angle of 172.61(11)° and B–I⋯I angle of 92.98(12)°.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

1,12-Diiodo-Ortho-Carborane: A Classic Textbook Example of the Dihalogen Bond

et al. 2021

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“…To assess their possible contribution to the stabilization of the observed conformation of complex 2 , we carried out its QTAIM (quantum theory of atoms in molecules) study [ 26 , 27 ]. Energy of intramolecular noncovalent interactions was estimated based on their correlation with the energy density function [ 28 ] that was found to be reliable for different types of weak noncovalent interactions [ 29 , 30 , 31 ]. Two CH⋯HB noncovalent contacts (shown in Figure 1 ) were observed (B5’-H5’⋯H3A-C3, 2.40Å, −2.4 kcal/mol; B8-H8⋯H7A-C7, 2.31Å, −2.6 kcal/mol).…”

Section: Resultsmentioning

confidence: 99%

The First Nickelacarborane with closo-nido Structure

et al. 2020

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The first nickelacarborane with closo-nido structure [10′,11′-(Py)2-3,9′-Ni(1,2-C2B9H11)(7′,8′-C2B8H8)] was isolated from the reaction of nickel(IV) bis(dicarbollide) with pyridine. The molecular structure of this complex was determined by single crystal X-ray diffraction. The nickel atom is a common vertex for the closo-NiC2B9 cluster and the nido-NC2B8 cluster where it is located together with carbon atoms in the open NiC2B2 pentagonal face. It is assumed that its formation proceeds through the nucleophile-induced removal of the B(6)H vertex followed by rearrangement of the forming 11-vertex cluster, which most likely proceeds through a sequence of closing and opening reactions.

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“…Calculated electron density of compound 4 was analyzed with AIM theory [ 69 ] using AIMAll program [ 70 ]. Energies of intramolecular noncovalent interactions were estimated using correlation between energy of a contact and potential energy density at bond critical point ( E = 1/2 V ( r )) [ 71 , 72 ] that is widely used for energetic analysis of noncovalent interactions [ 73 , 74 , 75 , 76 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Bis(Carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) and Attempt of Synthesis of Gadolinium Bis(Dicarbollide)

et al. 2021

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Bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) were prepared by the reactions of the corresponding carboranyl acyl chlorides with ethylenediamine. Crystal molecular structure of 1,1′-μ-(CH2NH(O)C-1,2-C2B10H11)2 was determined by single crystal X-ray diffraction. Treatment of bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 with ammonium or cesium fluoride results in partial deboronation of the ortho-carborane cages to the nido-carborane ones with formation of [7,7′(8′)-μ-(CH2NH(O)C(CH2)n-7,8-C2B9H11)2]2−. The attempted reaction of [7,7′(8′)-μ-(CH2NH(O)CCH2-7,8-C2B9H11)2]2− with GdCl3 in 1,2-dimethoxy- ethane did not give the expected metallacarborane. The stability of different conformations of Gd-containing metallacarboranes has been estimated by quantum-chemical calculations using [3,3-μ-DME-3,3′-Gd(1,2-C2B9H11)2]− as a model. It was found that in the most stable conformation the CH groups of the dicarbollide ligands are in anti,anti-orientation with respect to the DME ligand, while any rotation of the dicarbollide ligand reduces the stability of the system. This makes it possible to rationalize the design of carborane ligands for the synthesis of gadolinium metallacarboranes on their base.

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The influence of halogen type on structural features of compounds containing α-halo-α,α-dinitroethyl moieties

Cited by 34 publications

References 14 publications

1,12-Diiodo-Ortho-Carborane: A Classic Textbook Example of the Dihalogen Bond

1,12-Diiodo-Ortho-Carborane: A Classic Textbook Example of the Dihalogen Bond

The First Nickelacarborane with closo-nido Structure

Synthesis of Bis(Carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) and Attempt of Synthesis of Gadolinium Bis(Dicarbollide)

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