Ion-Pair Strain as the Driving Force for Hypervalent Adduct Formation between Iodide Ions and Substituted Iodobenzenes: Structural Alternatives to Meisenheimer Complexes

Weiß, Robert; Schwab, Oliver; Hampel, Frank

doi:10.1002/(sici)1521-3765(19990301)5:3<968::aid-chem968>3.3.co;2-c

Cited by 21 publications

(36 citation statements)

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“…We have noted previously ) that intramolecular interactions between mutually ortho I and nitro substituents on aryl rings appear to be repulsive, although intermolecular IÁ Á Ánitro interactions are generally attractive. The twist of the nitro group in (III), as well as those in (IV) and 2,4,6-trinitroiodobenzene (VI) [Cambridge Structural Database (CSD; Allen & Kennard, 1993) refcode ITNOBE01 (Weiss et al, 1999)], indicates repulsion between ortho I and nitro. It is interesting to note that in ITNOBE01 the CÐN distances for the 2-nitro and 4-nitro groups (the molecules lie on twofold rotation axes in space group P4 3 2 1 2) are 1.476 (9) A Ê and 1.451 (8) A Ê associated with nitro-group twist angles of 75.2 (9) and 7.8 (8) , respectively.…”

Section: Figurementioning

confidence: 99%

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

Garden

Fontes

Wardell

et al. 2002

Acta Crystallogr Sect B

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Molecules of 2-iodo-5-nitroaniline (I) are linked by N-H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic pi...pi stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo...nitro interactions into sheets of two types, each containing only a single type of molecule: pi...pi stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N-H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic pi...pi stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

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Section: Figurementioning

confidence: 99%

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

Garden

Fontes

Wardell

et al. 2002

Acta Crystallogr Sect B

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“…Part of the crystal structure of ITNOBE01 (Weiss et al, 1999) showing the formation of a linear [110] chain by means of a symmetric three-centre IÁ Á ÁO 2 N interaction. For the sake of clarity the unit-cell box is omitted.…”

Section: Figure 18mentioning

confidence: 99%

“…In 2,4,6-trinitroiodobenzene [(7); picryl iodide; CSD code ITNOBE01; Weiss et al, 1999], the molecules lie across twofold rotation axes in space group P4 3 2 1 2 (No. 96) and they are linked into strictly linear chains by symmetrical, planar three-centre IÁ Á ÁO 2 N interactions (Fig.…”

Section: Figure 18mentioning

confidence: 99%

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

Kelly

Skakle

Wardell

et al. 2001

Acta Crystallogr Sect B

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Molecules of N‐(4′‐iodophenylsulfonyl)‐4‐nitroaniline, 4‐O2NC6H4NHSO2C6H4I‐4′ (1), are linked by three‐centre I⋯O2N interactions into chains and these chains are linked into a three‐dimensional framework by C—H⋯O hydrogen bonds. In the isomeric N‐(4′‐nitrophenylsulfonyl)‐4‐iodoaniline, 4‐IC6H4NHSO2C6H4NO2‐4′ (2), the chains generated by the I⋯O2N interactions are again linked into a three‐dimensional framework by C—H⋯O hydrogen bonds. Molecules of N,N‐bis(3′‐nitrophenylsulfonyl)‐4‐iodoaniline, 4‐IC6H4N(SO2C6H4NO2‐3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I⋯O=S interactions: these chains are linked into sheets by a C—H⋯O hydrogen bond, and the sheets are linked into a three‐dimensional framework by aromatic π⋯π stacking interactions. In N‐(4′‐iodophenylsulfonyl)‐3‐nitroaniline, 3‐O2NC6H4NHSO2C6H4I‐4′ (4), there are rings formed by hard N—H⋯O=S hydrogen bonds and rings formed by two‐centre I⋯nitro interactions, which together generate a chain of fused rings: the combination of a C—H⋯O hydrogen bond and aromatic π⋯π stacking interactions links the chains into sheets. Molecules of N‐(4′‐iodophenylsulfonyl)‐4‐methyl‐2‐nitroaniline, 4‐CH3‐2‐O2NC6H3NHSO2C6H4I‐4′ (5), are linked by N—H⋯O=S and C—H⋯O(nitro) hydrogen bonds into a chain containing alternating and rings, but there are no I⋯O interactions of either type. There are two molecules in the asymmetric unit of N‐(4′‐iodophenylsulfonyl)‐2‐nitroaniline, 2‐O2NC6H4NHSO2C6H4I‐4′ (6), and the combination of an I⋯O=S interaction and a hard N—H⋯O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four‐component aggregate. C—H⋯O hydrogen bonds link these four‐molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

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“…For example, halogenÁ Á Áhalide (C-YÁ Á ÁX À , X and Y = Cl, Br or I) synthons do play a important role in determining the crystal structure of halogenated pyridinium salts [40][41][42][43][44] and other crystal structures, such as diphenyl dichlorophosphonium trichloride-chlorine solvate mixture [45], tetrahalometalate (II) ions [46][47][48][49][50], and 1,2-dibromohexafluoropropane [51] Recently, there has been renewed interest in the area of perfluorocarbon (PFC) compounds; this is mainly ascribed to the unique properties of PFCs, such as low surface energy, low affinity for hydrocarbon (HC) parents, and immiscibility with water [52]. Owing to the very strong electron-withdrawing ability of fluorine atoms and perfluorine residues, halo-perfluorocarbons (halo-PFCs) are much stronger halogen bond donors than corresponding halo-hydrocarbon (halo-HC) parents and present numerous applications in many fields of chemistry [3,9,53,54].…”

Section: Introductionmentioning

confidence: 99%

Understanding the magnitude and origin of bidentate charge-assisted halogen bonds of halo-perfluorocarbons and halo-hydrocarbons with halide anions

Shi¹,

Lu²,

Fan³

et al. 2008

Journal of Molecular Structure: THEOCHEM

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Ion-Pair Strain as the Driving Force for Hypervalent Adduct Formation between Iodide Ions and Substituted Iodobenzenes: Structural Alternatives to Meisenheimer Complexes

Cited by 21 publications

References 0 publications

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

Understanding the magnitude and origin of bidentate charge-assisted halogen bonds of halo-perfluorocarbons and halo-hydrocarbons with halide anions

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